Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 13225-19-9
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 462.543
• Mol file: 13225-19-9.mol

Synonyms:Glucopyranoside,methyl 2,3-di-O-benzyl-4,6-O-benzylidene-, a-D- (8CI); Pyrano[3,2-d]-1,3-dioxin, a-D-glucopyranoside deriv.

Chemical Property of Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

• Melting Point: 95.5 - 96 °C
• PSA: 55.38000
• LogP: 4.64270

Purity/Quality:

97% ^*data from raw suppliers

Methyl 4,6-O-benzylidene-2,3-di-O-benzyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside

There total 78 articles about Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-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: 99.0%

benzyl bromide (100-39-0) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,13225-19-9,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1039/c4ra11035h

Reference yield: 98.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,13225-19-9,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 60 ℃; for 0.166667h; regioselective reaction; Sonication; Inert atmosphere;

DOI:10.1039/c2ob25452b

Reference yield: 96.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + benzyl bromide (100-39-0) → methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9)

Guidance literature:

methyl 4,6-O-benzylidene-α-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2017.05.012

upstream raw materials:

benzyl chloride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

tetrachloromethane

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside

Downstream raw materials:

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzoylglucopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

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