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

Base Information

• Chemical Name: methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside
• CAS No.: 177554-76-6
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• Mol file: 177554-76-6.mol

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

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

There total 7 articles about methyl 3-O-benzyl-2-deoxy-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: 67.0%

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 (177554-75-5) → methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (177554-76-6)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1139/v96-036

Reference yield:

C15H20O6 + benzyl bromide (100-39-0) → methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside + methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (177554-76-6)

Guidance literature:

C₁₅H₂₀O₆; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h; optical yield given as %de;

DOI:10.1016/j.carres.2011.10.025

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (177554-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) di-n-butyltin oxide; 2.) tetra-n-butylammonium fluoride, 4 Angstroem molecular sieves / 1.) benzene, reflux, 4 h; 2.) benzene, RT, overnight

2: sodium hydride, imidazole / tetrahydrofuran / 1.5 h

3: 67 percent / tributyltin hydride / toluene / Heating

With 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1139/v96-036

upstream 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

benzyl bromide

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

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

Downstream raw materials:

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

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