(4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 148102-27-6
• Molecular Formula: C₂₉H₅₄N₂O₇S
• Molecular Weight: 574.823

Synonyms:

Chemical Property of (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 5 articles about (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-hydroxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (134916-03-3) + methanesulfonyl chloride (124-63-0) → (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (148102-27-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

(S)-2-methylbutylamine (34985-37-0) → (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (148102-27-6)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC, HOBT

2: 1) BH₃*THF 2) 1N NaOH, H₂O₂

3: Et₃N / CH₂Cl₂ / 0 °C

With sodium hydroxide; borane-THF; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

(4S,5S)-5-((S)-1-Carboxy-pent-4-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (148102-24-3) → (4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-methanesulfonyloxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (148102-27-6)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC, HOBT

2: 1) BH₃*THF 2) 1N NaOH, H₂O₂

3: Et₃N / CH₂Cl₂ / 0 °C

With sodium hydroxide; borane-THF; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)74351-6

upstream raw materials:

(4S,5S)-4-Cyclohexylmethyl-5-[(S)-5-hydroxy-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

methanesulfonyl chloride

(S)-2-methylbutylamine

(4S,5S)-5-((S)-1-Carboxy-pent-4-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-4-[(1S,2S,3S)-7-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-heptylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester

{(S)-1-[(3S,12S,13S,14S)-14-Cyclohexylmethyl-13-hydroxy-12-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotetradec-3-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

(4S,5S)-5-[(S)-5-Benzyloxycarbonylamino-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-5-[(S)-5-Azido-1-((S)-2-methyl-butylcarbamoyl)-pentyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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