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CAS 74-86-2
Acetyleneethyne
Codes: Tazobactam Sodium-010, Astaxanthin-016, ETON-008
Application context (from source-drug indications)
Intra-abdominal infectionTazobactam Sodium/CeftolozaneVentilator-associated pneumoniaTazobactam Sodium/CeftolozaneUrinary tract infectionTazobactam Sodium/CeftolozaneCommunity-acquired bacterial pneumoniaTazobactam Sodium/CeftolozanePyelonephritisTazobactam Sodium/CeftolozaneHospital-acquired pneumoniaTazobactam Sodium/CeftolozaneBacterial infectionCeftazidime/Tazobactam SodiumRespiratory tract infectionCeftazidime/Tazobactam SodiumUrinary tract infectionCeftazidime/Tazobactam SodiumBacterial infectionTazobactam Sodium营养失调AstaxanthinKnee arthritisAstaxanthinDiabetic neuropathyAstaxanthinStrokeAstaxanthinContraceptionEtonogestrelAcquired immunodeficiency syndromeEtonogestrelDysmenorrhoeaEtonogestrel血崩EtonogestrelBenign prostatic hyperplasiaEtonogestrel月经失调Etonogestrel
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Tazobactam Sodium/Ceftolozane | Tier C — Watch / trade | - |
| Ceftazidime/Tazobactam Sodium | Tier C — Watch / trade | - |
| Tazobactam Sodium | Tier C — Watch / trade | - |
| Astaxanthin | Tier C — Watch / trade | - |
| Etonogestrel | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-Trimethylsilylethyne→Benzhydryl 2a-methyl-2beta-(4-trimethylsilyl-1,2,3-triazol-1 ylmethyl)penam-3a-carboxylate-1,1-dioxide→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→Acetylene→1-Acetoxyethylene→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-Trimethylsilylethyne→Benzhydryl 2a-methyl-2beta-(4-trimethylsilyl-1,2,3-triazol-1 ylmethyl)penam-3a-carboxylate-1,1-dioxide→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→Acetylene→1-Acetoxyethylene→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1-Trimethylsilylethyne→Benzhydryl 2a-methyl-2beta-(4-trimethylsilyl-1,2,3-triazol-1 ylmethyl)penam-3a-carboxylate-1,1-dioxide→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→Acetylene→1-Acetoxyethylene→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(+)-6-Aminopenicillanic acid→(2S,5R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid→(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→(Diphenylmethylidene)hydrazine→[Diazo(phenyl)methyl]benzene→(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,5R,6S)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,5R)-2beta-[(Benzhydryloxy)carbonyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4-oxide→1,3-Benzothiazole-2-thiol→(2R)-2-[(2R)-2-[(Benzothiazol-2-yl)dithio]-4-oxoazetidin-1-yl]-3-methyl-3-butenoic acid benzhydryl ester→(2S-(2alpha,3beta,5alpha))-3-(Chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid diphenylmethyl ester→Diphenylmethyl (2S,3R,4R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Diphenylmethyl (2S,3S,4R,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Diphenylmethyl (2R,3S,6R)-3-azido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate→Benzhydryl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,4R,6S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide→1-(Chloromethyl)-3,5-dinitrobenzene→1-Methyl-3,5-dinitrobenzene→Benzyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,4R,5R)-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→1,3-Benzothiazole-2-thiol→Benzyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→(3,5-Dinitrophenyl)methyl (2R)-2-[(2R)-2-[(1,3-benzothiazol-2-yl)disulfanyl]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate→Benzyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3R,5R)-3-(chloromethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Benzyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-(azidomethyl)-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→Acetylene→Benzyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(3,5-Dinitrophenyl)methyl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate→(2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-Hydroxy-3-[(1E)-3-hydroxy-3-methylpenta-1,4-dien-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one→Acetylene→1-Buten-3-one→Lithium 3-methylpent-1-en-4-yn-3-olate→Dilithium 3-methylpent-4-en-1-yn-1-id-3-olate→2,2,4,6,6-Pentamethyl-7,7a-dihydro-1,3-benzodioxol-5-one→Dilithium 2,2,4,6,6-pentamethyl-5-(3-methyl-3-oxidopent-4-en-1-yn-1-yl)-5,6,7,7a-tetrahydro-2H-1,3-benzodioxol-5-olate→6-Hydroxy-3-(3-hydroxy-3-methylpent-4-en-1-yn-1-yl)-2,4,4-trimethylcyclohex-2-en-1-one→6-Hydroxy-3-[(1E)-3-hydroxy-3-methylpenta-1,4-dien-1-yl]-2,4,4-trimethylcyclohexa-2,5-dien-1-one
1-Chloroethylene→Chlorido(ethenyl)magnesium→Acetylene→1-Buten-3-one→(2E)-3-Methylpent-2-en-4-yn-1-ol→2-Hydroxyethyl methyl ketone→(Ethynyl)magnesium bromide→3-Methylpent-4-yne-1,3-diol
(8S,9S,10R,11R,13S,14S)-13-ethyl-11-hydroxy-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione→(8'S,9'S,10'R,13'S,14'S)-13'-ethyl-1',2',6',7',8',9',10',12',13',14',15',16'-dodecahydro-11'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolan]-11'-one→methyltriphenylphosphonium bromide→(8'S,9'S,10'R,13'S,14'S)-13'-ethyl-11'-methylene-1',6',7',8',9',10',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,3'-cyclopenta[a]phenanthrene-17',2''-[1,3]dioxolane]→(8S,9S,10R,13S,14S)-13-ethyl-11-methylene-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione→pyrrolidine→(8S,9S,10R,13S,14S)-13-ethyl-11-methylene-3-(pyrrolidin-1-yl)-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-one→ethyne→(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-3-(pyrrolidin-1-yl)-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
(8S,9S,10R,11R,13S,14S)-13-ethyl-11-hydroxy-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione→ethyne→(8S,9S,10R,11R,13S,14S)-13-ethyl-11-hydroxy-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dithiolan]-17(2H)-one→(8'S,9'S,10'R,11'R,13'S,14'S)-13'-ethyl-1',6',7',8',9',10',11',12',13',14',15',16'-dodecahydro-2'H-dispiro[[1,3]dioxolane-2,17'-cyclopenta[a]phenanthrene-3',2''-[1,3]dithiolan]-11'-ol→(8'S,9'S,10'R,13'S,14'S)-13'-ethyl-1',2',6',7',8',9',10',12',13',14',15',16'-dodecahydro-11'H-dispiro[[1,3]dioxolane-2,17'-cyclopenta[a]phenanthrene-3',2''-[1,3]dithiolan]-11'-one→(8S,9S,10R,13S,14S)-13-ethyl-11-methylene-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dithiolan]-17(2H)-one→(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dithiolan]-17-ol
(8S,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-11-methylene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one→(8S,9S,10R,13S,14S)-13-ethyl-11-methylene-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione→pyrrolidine→(8S,9S,10R,13S,14S)-13-ethyl-11-methylene-3-(pyrrolidin-1-yl)-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-one→ethyne→(13S,14S,17S)-13-ethyl-17-hydroxy-3-methoxy-6,7,12,13,14,15,16,17-octahydro-11H-cyclopenta[a]phenanthren-11-one→(11S,13S,14S,17S)-13-ethyl-3-methoxy-11-((trimethylsilyl)methyl)-7,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-11,17-diol→(8S,9S,11S,13S,14S,17S)-13-ethyl-3-methoxy-11-((trimethylsilyl)methyl)-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-11,17-diol
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