methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside
• CAS No.: 362608-64-8
• Molecular Formula: C₇₇H₈₆O₁₆
• Molecular Weight: 1267.52
• Mol file: 362608-64-8.mol

Synonyms:methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

Chemical Property of methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

There total 15 articles about methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside 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: 83.0%

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6) + methyl 2-O-benzoyl-(6-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2'-O-p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside (362608-61-5) → methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside (362608-64-8)

Guidance literature:

With 2,6-di-O-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1560/YXQT-2JJU-YLAA-L04Q

Reference yield:

benzyl bromide (100-39-0) → methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside (362608-64-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / sodium hydride / dimethylformamide / 1 h / 20 °C

2: di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / 0.5 h

3: 93 percent / sodium methoxide; MeOH / 2 h / 20 °C

4: 83 percent / 2,6-di-tert-O-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

With methanol; di-tert-butyl-4-methylpyridine; 2,6-di-O-tert-butyl-4-methylpyridine; sodium methylate; sodium hydride; methyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1560/YXQT-2JJU-YLAA-L04Q

Reference yield:

p-methoxybenzyl chloride (824-94-2) → methyl 6-O-benzyl-4-O-(p-methoxybenzyl)-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(2'-O-(p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside (362608-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / dimethylformamide / 0.33 h

1.2: 91 percent / dimethylformamide / 2 h / 0 °C

2.1: 81 percent / 48 percent aq. HBF₄ / methanol / 48 h / 0 - 20 °C

3.1: camphorsulphonic acid / CHCl₃

3.2: 88 percent / 80 percent aq. AcOH / 1 h / 20 °C

4.1: di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / 0.5 h

5.1: 93 percent / sodium methoxide; MeOH / 2 h / 20 °C

6.1: 83 percent / 2,6-di-tert-O-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

With methanol; tetrafluoroboric acid; di-tert-butyl-4-methylpyridine; 2,6-di-O-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; sodium methylate; sodium hydride; methyl trifluoromethanesulfonate; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1560/YXQT-2JJU-YLAA-L04Q

upstream raw materials:

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

methyl 2-O-benzoyl-(6-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2'-O-p-methoxybenzyl)-4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

benzyl bromide

methyl 2,3-O-isopropylidene-6-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

methyl 6-O-benzyl-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-α-D-mannopyranoside

methyl 6-O-benzyl-2-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-3-O-(4'-O-benzyl-3',6'-dideoxy-α-D-xylo-hexopyranosyl)-4,2'-di-O-methylene-α-D-mannopyranoside