(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

Base Information

• Chemical Name: (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
• CAS No.: 934482-17-4
• Molecular Formula: C₄₆H₆₁NO₁₆
• Molecular Weight: 883.987
• Mol file: 934482-17-4.mol

Synonyms:(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

Chemical Property of (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

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-(2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

There total 3 articles about (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 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: 18.0%

2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate + (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-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (934482-17-4)

Guidance literature:

With trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ja066633g

Reference yield:

benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate (7622-21-1) → (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 (934482-17-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: dibutyltin oxide / benzene

2.2: CsF / 1,2-dimethoxy-ethane

3.1: 18 percent / molecular sieves 4 Angstroem; TfOH / CH₂Cl₂ / 3 h / 20 °C

With trifluorormethanesulfonic acid; 4 A molecular sieve; lutidine; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1021/ja066633g

Reference yield:

(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester (146953-71-1) → (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 (934482-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / benzene

1.2: CsF / 1,2-dimethoxy-ethane

2.1: 18 percent / molecular sieves 4 Angstroem; TfOH / CH₂Cl₂ / 3 h / 20 °C

With trifluorormethanesulfonic acid; 4 A molecular sieve; di(n-butyl)tin oxide; In dichloromethane; benzene;

DOI:10.1021/ja066633g

upstream raw materials:

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

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

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

Downstream raw materials:

(1S,2S,4R,5S)-4-((R)-1-carboxy-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