benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate

Base Information

• Chemical Name: benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate
• CAS No.: 389607-72-1
• Molecular Formula: C₂₉H₃₅NO₁₄
• Molecular Weight: 621.595
• Mol file: 389607-72-1.mol

Synonyms:

Chemical Property of benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate

There total 5 articles about benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate 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: 94.0%

(1R,2R,3S,5S)-2-isocyanato-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octan-7-one (153946-32-8) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate (389607-72-1)

Guidance literature:

In benzene; for 20h; Heating;

DOI:10.1039/b105374b

Reference yield:

(1R,2R,3S)-5-oxo-3-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>cyclohexane-1,2-dicarboxylic anhydride (104629-48-3) → benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate (389607-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / NaBH₃CN; glacial acetic acid / 15 h

2: (COCl)2; DMF / CH₂Cl₂ / 20 °C

3: 4.24 g / NaN₃ / tetrahydrofuran / 1 h / 0 °C

4: 98 percent / benzene / 2 h / Heating

5: 94 percent / benzene / 20 h / Heating

With sodium azide; oxalyl dichloride; sodium cyanoborohydride; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; benzene; 4: Curtius rearrangement;

DOI:10.1039/b105374b

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1R,2R,3S,5S)-2-chlorocarbonyl-7-oxo-6-oxa-bicyclo[3.2.1]oct-3-yloxy)-tetrahydro-pyran-3-yl ester → benzyl (1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carbamate (389607-72-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 4.24 g / NaN₃ / tetrahydrofuran / 1 h / 0 °C

2: 98 percent / benzene / 2 h / Heating

3: 94 percent / benzene / 20 h / Heating

With sodium azide; In tetrahydrofuran; benzene; 2: Curtius rearrangement;

DOI:10.1039/b105374b

upstream raw materials:

(1R,2R,3S,5S)-2-isocyanato-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octan-7-one

benzyl alcohol

(1R,2R,3S)-5-oxo-3-<(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy>cyclohexane-1,2-dicarboxylic anhydride

(1R,2R,3S,5S)-7-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-oxabicyclo[3.2.1]octane-2-carboxylic acid