(2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

Base Information

• Chemical Name: (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol
• CAS No.: 197777-97-2
• Molecular Formula: C₂₉H₃₆ClNO₆
• Molecular Weight: 530.061
• Mol file: 197777-97-2.mol

Synonyms:(2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

Chemical Property of (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

There total 5 articles about (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol 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: 84.0%

acetic anhydride (108-24-7) + 3-[(4-benzyloxy-3-chloro-phenyl)-hydroxy-methyl]-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester (197778-01-1) → (2S,3R)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol (197777-86-9) + (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol (197777-97-2)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

2-monochlorophenol (95-57-8) → (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol (197777-97-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bromine / tetrachloromethane / 12 h / 20 °C

2.1: potassium carbonate / acetone / 2 h / Heating

3.1: magnesium / tetrahydrofuran / 1 h / 20 °C

3.2: 13 / 1 h / 0 °C

4.1: pyridine / dichloromethane / 2 h / 20 °C

With pyridine; bromine; potassium carbonate; magnesium; In tetrahydrofuran; tetrachloromethane; dichloromethane; acetone; 1.1: Bromination / 2.1: Benzylation / 3.1: Metallation / 3.2: Grignard reaction / 4.1: Acetylation;

Reference yield:

4-bromo-2-chlorophenol (3964-56-5) → (2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol (197777-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / acetone / 2 h / Heating

2.1: magnesium / tetrahydrofuran / 1 h / 20 °C

2.2: 13 / 1 h / 0 °C

3.1: pyridine / dichloromethane / 2 h / 20 °C

With pyridine; potassium carbonate; magnesium; In tetrahydrofuran; dichloromethane; acetone; 1.1: Benzylation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Acetylation;

upstream raw materials:

acetic anhydride

(S)-Garner's aldehyde

3-[(4-benzyloxy-3-chloro-phenyl)-hydroxy-methyl]-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester

2-monochlorophenol

Downstream raw materials:

((1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-2-(3-chloro-4-hydroxy-phenyl)-1-{(S)-2-cyano-1-[(R)-1-(3-fluoro-4-nitro-phenyl)-2-methoxy-ethylcarbamoyl]-ethylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester

(2R,3R)-3-(4-Benzyloxy-3-chloro-phenyl)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

(2R,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid

(S)-3-[(S)-(4-Benzyloxy-3-chloro-phenyl)-hydroxy-methyl]-1-oxa-4-aza-spiro[4.5]decane-4-carboxylic acid tert-butyl ester