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CAS 27144-18-9

3-(Tritylsulfanyl)propanoic acidS-(Trityl)-mercapto propionic acid3-(tritylthio)propanoic acid

Codes: Atosiban-021, EPTI-013

Application context (from source-drug indications)

产科分娩(早产)Atosiban acetate早产(孕37周前)Atosiban acetateEndometriosisAtosiban acetateUnstable anginaEptifibatideMyocardial infarctionEptifibatideIschaemic strokeEptifibatideAcute coronary syndromeEptifibatideSickle cell diseaseEptifibatideST段抬高型心肌梗死Eptifibatide

Source drugs (routes using this intermediate)

DrugTierExpiry
Atosiban acetateTier C — Watch / trade-
EptifibatideTier 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.

Atosiban acetateOptimised routesteps: 5total yield: 0.838g(Atosiban-023)
Resin bound N-[(2S,5S)-2-[(2S)-butan-2-yl]-5-(4-ethoxybenzyl)-4,7-dioxo-9-(tritylsulfanyl)nonanoyl]-O-tert-butyl-L-threonyl-N-trityl-L-asparaginyl-S-trityl-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamid→Resin bound N-[(2S,5R)-5-amino-2-[(2S)-butan-2-yl]-6-(4-ethoxyphenyl)-4-oxohexanoyl]-O-tert-butyl-L-threonyl-N-trityl-L-asparaginyl-S-trityl-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→3-(Tritylsulfanyl)propanoic acid→Resin bound 1-([(4R,7S,10S,13S,16S)-13-[(2S)-butan-2-yl]-10-[(1R)-1-tert-butoxyethyl]-16-(4-ethoxybenzyl)-6,9,12,15,18-pentaoxo-7-[2-oxo-2-(tritylamino)ethyl]-1,2-dithia-5,8,11-triazacycloicosan-4-yl]carbonyl)-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycinamide→1-[(4R,7S,10S,13S,16S)-7-(2-Amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11-triazacycloicosane-4-carbonyl]-L-prolyl-L-ornithylglycinamide<-fgf->1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin<-fgf->1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin
Atosiban acetateOptimised routesteps: 2total yield: /
O-Ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-O-tert-butyl-L-threonyl-N-(triphenylmethyl)-L-asparaginyl-S-(acetamidomethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine→CTC resin bound O-ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-O-tert-butyl-L-threonyl-N-(triphenylmethyl)-L-asparaginyl-S-(acetamidomethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine→3-(Tritylsulfanyl)propanoic acid→CTC resin bound O-ethyl-D-tyrosyl-L-isoleucyl-O-tert-butyl-L-threonyl-N-(triphenylmethyl)-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-(tert-butoxycarbonyl)-L-ornithylglycine
Atosiban acetateOptimised routesteps: 3total yield: /
Resin bound O-ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→Resin bound L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→Resin bound O-ethyl-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→S-(Trityl)-mercapto propionic acid→Resin bound L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-isoleucine→O-Ethyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine
Atosiban acetateOptimised routesteps: 3total yield: /
O-Ethyl-D-tyrosine→O-Ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosine→Resin bound O-ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→Resin bound L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-L-ornithylglycinamide→S-(Trityl)-mercapto propionic acid
Atosiban acetateOptimised routesteps: 3total yield: /
Resin bound O-ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide<-fgf->Resin bound Mpa(Trt)-D-Tyr(Et)-Ile-Thr-Asn-Cys( Trt)-Pro-Orn(Dde)-Gly→Resin bound Ile-Thr-Asn-Cys( Trt)-Pro-Orn(Dde)-Gly→Resin bound O-ethyl-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide<-fgf->Resin bound D-Tyr(Et)-Ile-Thr-Asn-Cys(Trt)-Pro-Orn(Dde)-Gly→3-(Tritylsulfanyl)propanoic acid→Resin bound Thr-Asn-Cys(Trt)-Pro-Orn(Dde)-Gly→N-[[(9H-Fluoren-9-yl)methoxy]carbonyl]-L-isoleucine→O-Ethyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine
Atosiban acetateOptimised routesteps: 3total yield: /
O-Ethyl-D-tyrosine→O-Ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosine→Resin bound O-ethyl-N-[3-[(triphenylmethyl)sulfanyl]propanoyl]-D-tyrosyl-L-isoleucyl-L-threonyl-L-asparaginyl-S-(triphenylmethyl)-L-cysteinyl-L-prolyl-N5-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]-L-ornithylglycinamide<-fgf->Resin bound Mpa(Trt)-D-Tyr(Et)-Ile-Thr-Asn-Cys( Trt)-Pro-Orn(Dde)-Gly→Resin bound Ile-Thr-Asn-Cys( Trt)-Pro-Orn(Dde)-Gly→3-(Tritylsulfanyl)propanoic acid
EptifibatideOriginator routesteps: 8total yield: /
(7S,13S)-tert-butyl 13-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamoyl)-7-(4-aminobutyl)-5,8,11-trioxo-1,1,1-triphenyl-2-thia-6,9,12-triazapentadecan-15-oate→3,5-dimethyl-1H-pyrazole-1-carboximidamide→N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine→(9H-fluoren-9-yl)methyl (R)-(1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamate→(((9H-fluoren-9-yl)methoxy)carbonyl)-L-proline→(9H-fluoren-9-yl)methyl (S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carboxylate→Na-(((9H-fluoren-9-yl)methoxy)carbonyl)-1-(tert-butoxycarbonyl)-L-tryptophan→(9H-fluoren-9-yl)methyl ((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamate→(S)-tert-butyl 4-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-oxobutanoate→(((9H-fluoren-9-yl)methoxy)carbonyl)glycine→(S)-tert-butyl 4-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)amino)-3-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)acetamido)-4-oxobutanoate→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanoic acid→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→(10S,16S)-tert-butyl 16-(((S)-3-(1H-indol-3-yl)-1-((S)-2-(((R)-1-(methylamino)-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-1-oxopropan-2-yl)carbamoyl)-10-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaoctadecan-18-oate→3-(tritylthio)propanoic acid
EptifibatideOptimised routesteps: 9total yield: /
(((9H-fluoren-9-yl)methoxy)carbonyl)-L-proline→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→3-(tritylthio)propanoic acid→methyl glycinate hydrochloride→(S)-2-(((benzyloxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanoic acid→(S)-methyl 2-(2-(((benzyloxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)hexanamido)acetate→(S)-methyl 2-(6-((tert-butoxycarbonyl)amino)-2-(3-(tritylthio)propanamido)hexanamido)acetate→(S)-tert-butyl 3-amino-4-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-4-oxobutanoate→(10S,16S)-tert-butyl 16-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamoyl)-2,2-dimethyl-4,11,14-trioxo-10-(3-(tritylthio)propanamido)-3-oxa-5,12,15-triazaoctadecan-18-oate→2-((3R,11S,17S,20S,25aS)-20-((1H-indol-3-yl)methyl)-11-(4-aminobutyl)-3-carbamoyl-1,9,12,15,18,21-hexaoxodocosahydro-1H-pyrrolo[2,1-g][1,2,5,8,11,14,17,20]dithiahexaazacyclotricosin-17-yl)acetic acid hydrochloride→amino(imino)methanesulfonic acid hydrate→(R)-2-amino-3-(tritylthio)propanamide→(S)-(9H-fluoren-9-yl)methyl 2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidine-1-carboxylate→(((9H-fluoren-9-yl)methoxy)carbonyl)-L-tryptophan→(9H-fluoren-9-yl)methyl ((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamate→(S)-tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-4-oxobutanoate
EptifibatideOptimised routesteps: 6total yield: /
N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine→(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid→3-(tritylthio)propanoic acid→(S)-pyrrolidine-2-carboxylic acid→(S)-tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(((S)-1-((S)-2-(((R)-1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamoyl)pyrrolidin-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)amino)-4-oxobutanoate→L-cysteine hydrochloride→(R)-(9H-fluoren-9-yl)methyl (1-amino-1-oxo-3-(tritylthio)propan-2-yl)carbamate→(2R,3R)-2,3-dihydroxysuccinic acid→(R)-2-amino-3-(tritylthio)propanamide (2R,3R)-2,3-dihydroxysuccinate→(R)-1-((S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylic acid→EPTI-057→EPTI-058→(S)-2-amino-3-(1H-indol-3-yl)propanoic acid→(S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoic acid→3-bromoprop-1-ene→(R)-2-allyl 1-tert-butyl pyrrolidine-1,2-dicarboxylate→(R)-allyl 1-((S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→(R)-allyl 1-((S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanamido)-3-(1H-indol-3-yl)propanoyl)pyrrolidine-2-carboxylate→EPTI-065→EPTI-066→EPTI-067

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