allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

Base Information

Chemical Name:allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside
CAS No.:1443672-42-1
Molecular Formula:C₅₇H₅₈O₁₂
Molecular Weight:935.08
Hs Code.:

Synonyms:allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

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Chemical Property of allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

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Technology Process of allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

There total 3 articles about allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside 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: 71.0%

: 1443672-41-0
allyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

: 159407-17-7
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1443672-42-1
allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

allyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo4005266

Reference yield:

: 137172-47-5
allyl 3-O-benzyl-(R)-4,6-O-benzylidene-β-D-glucopyranoside

: 1443672-42-1
allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 10 h / 20 °C

2.1: trifluoroacetic acid; triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C

3.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.08 h / -60 °C / Molecular sieve; Inert atmosphere

3.2: -78 - 20 °C

With triethylsilane; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In pyridine; dichloromethane;
DOI:10.1021/jo4005266

Reference yield:

: 98-88-4
benzoyl chloride

: 1443672-42-1
allyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 10 h / 20 °C

2.1: trifluoroacetic acid; triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C

3.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.08 h / -60 °C / Molecular sieve; Inert atmosphere

3.2: -78 - 20 °C

With triethylsilane; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In pyridine; dichloromethane;
DOI:10.1021/jo4005266