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CAS 76859-48-8

Methyl 6,8-di-O-benzyl-2,3,7-trideoxy-3-formyl-5-O-methyl-D-ido-octofuranoside

Codes: Josamycin-015

Application context (from source-drug indications)

Bacterial infectionJosamycin PropionateInflammatory diseaseJosamycin Propionate

Source drugs (routes using this intermediate)

DrugTierExpiry
Josamycin PropionateTier 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.

Josamycin PropionateOptimised routesteps: 13total yield: /
(3aR,5S,6S,6aR)-5-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol→(3aS,5S,6R,6aS)-5-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole→1,2-O-Isopropylidene-3-O-methyl-alpha-L-glucofuranose→6-O-Benzoyl-1,2-O-isopropylidene-3-O-methyl-alpha-L-glucofuranose→6-O-Benzoyl-1,2-O-isopropylidene-3-O-methyl-5-O-[(4-methylphenyl)sulfonyl]-alpha-L-glucofuranose→5-Deoxy-1,2-O-isopropylidene-3-O-methyl-alpha-L-xylo-hexofuranose→(Carbomethoxymethylene)triphenylphosphorane→Methyl (2E)-2,3,7-trideoxy-5-O-methyl-D-xylo-oct-2-enonate→Methyl (2E)-2,3,7-trideoxy-4,6-O-isopropylidene-8-O-(methoxymethyl)-5-O-methyl-D-xylo-oct-2-enonate→Methyl (4xi)-2,3,7-trideoxy-4,6-O-isopropylidene-8-O-(methoxymethyl)-5-O-methyl-3-[(methylsulfanyl)(methylsulfinyl)methyl]-D-lyxo-octonate→(4R,5S)-5-[(1S,2R)-2,4-Dihydroxy-1-methoxybutyl]-4-[(ethylsulfanyl)(methylsulfanyl)methyl]dihydrofuran-2(3H)-one→2,3,7-Trideoxy-3-[(ethylsulfanyl)(methylsulfanyl)methyl]-5-O-methyl-D-ido-octofuranose→Methyl 2,3,7-trideoxy-3-[(ethylsulfanyl)(methylsulfanyl)methyl]-5-O-methyl-D-ido-octofuranoside→Methyl 6,8-di-O-benzyl-2,3,7-trideoxy-3-[(ethylsulfanyl)(methylsulfanyl)methyl]-5-O-methyl-D-ido-octofuranoside→Methyl 6,8-di-O-benzyl-2,3,7-trideoxy-3-formyl-5-O-methyl-D-ido-octofuranoside
Josamycin PropionateOptimised routesteps: 8total yield: /
Methyl 6,8-di-O-benzyl-2,3,7-trideoxy-3-formyl-5-O-methyl-D-ido-octofuranoside→3-(Triphenylphosphoranylidene)butan-2-one→1-Acetyl-1-chloroethane→Methyl 6,8-di-O-benzyl-2,3,7-trideoxy-5-O-methyl-3-[(1Z)-2-methyl-3-oxobut-1-en-1-yl]-D-ido-octofuranoside→Methyl 2,3,7-trideoxy-5-O-methyl-3-(2-methyl-3-oxobutyl)-D-ido-octofuranoside→Methyl 2,3,7-trideoxy-5-O-methyl-3-(2-methyl-3-oxobutyl)-D-ido-octofuranosiduronic acid→Dimethyl 2,3,7-trideoxy-5-O-methyl-3-[(2R)-2-methyl-3-oxobutyl]-D-ido-octofuranosiduronate→(2E)-5-Hydroxyhex-2-enal→Dimethyl 2,3,7-trideoxy-3-[(2R,4E,6E,9R)-9-hydroxy-2-methyl-3-oxodeca-4,6-dien-1-yl]-5-O-methyl-D-ido-octofuranosiduronate→Methyl 2,3,7-trideoxy-3-[(2R,4E,6E,9R)-3,9-dihydroxy-2-methyldeca-4,6-dien-1-yl]-5-O-methyl-D-ido-octofuranosiduronic acid→Methyl S-phenyl 2,3,7-trideoxy-3-[(2R,4E,6E,9R)-3,9-dihydroxy-2-methyldeca-4,6-dien-1-yl]-5-O-methyl-8-thio-D-ido-octofuranosiduronate

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