methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside
• CAS No.: 162583-80-4
• Molecular Formula: C₂₂H₂₆O₇
• Molecular Weight: 402.444
• Mol file: 162583-80-4.mol

Synonyms:methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

There total 3 articles about methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-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: 54.0%

benzyl bromide (100-39-0) + methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside (162680-20-8) → methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (162583-80-4) + methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (162583-81-5)

Guidance literature:

With tetrabutylammomium bromide; di(n-butyl)tin oxide; In acetonitrile; for 18h; regioselective reaction; Molecular sieve; Reflux;

DOI:10.1016/j.tetasy.2009.03.006

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (162583-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / p-toluenesulfonic acid / dimethylformamide / 70 °C

2: 1.) n-Bu₂SnO, n-Bu₄NI, 4A molecular sieves / 1.) CH₃CN, reflux, 2 h, 2.) CH₃CN, reflux, 16 h

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja00116a046

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 3-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (162583-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / p-toluenesulfonic acid / dimethylformamide / 70 °C

2: 1.) n-Bu₂SnO, n-Bu₄NI, 4A molecular sieves / 1.) CH₃CN, reflux, 2 h, 2.) CH₃CN, reflux, 16 h

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja00116a046

upstream raw materials:

benzyl bromide

methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

methyl-alpha-D-glucopyranoside

Downstream raw materials:

Dithiocarbonic acid O-[(2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl] ester S-methyl ester

methyl 3-O-benzyl-2-deoxy-4-O-(p-methoxybenzyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-arabino-hexopyranoside

methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside

[(2R,3S,4R,6S)-4-Benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol