(1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• CAS No.: 875799-03-4
• Molecular Formula: C₃₂H₄₂O₈
• Molecular Weight: 554.681
• Mol file: 875799-03-4.mol

Synonyms:(1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Chemical Property of (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

There total 2 articles about (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-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: 30.0%

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester (146953-71-1) + (1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (221344-09-8) → (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (875799-03-4)

Guidance literature:

(1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester; With di(n-butyl)tin oxide; In benzene; Heating;

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester; With cesium fluoride; In 1,2-dimethoxyethane;

DOI:10.1016/j.bmcl.2003.07.007

Reference yield:

benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate (7622-21-1) → (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (875799-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / lutidine / CH₂Cl₂ / 0.33 h / 20 °C

2.1: dibutyltin oxide / benzene

2.2: CsF / 1,2-dimethoxy-ethane

With lutidine; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1021/ja066633g

Reference yield: 45.0%

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (92052-29-4) + (1S,2S,4R,5S)-4-((R)-1-Benzyloxycarbonyl-2-phenyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (875799-03-4) → (1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (934482-15-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -30 ℃; for 3h;

DOI:10.1021/ja066633g

upstream raw materials:

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester

(1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate

Downstream raw materials:

4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-2-phenyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

(1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

(1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

(1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester