methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 241471-12-5
• Molecular Formula: C₄₉H₅₂O₁₁
• Molecular Weight: 816.945
• Mol file: 241471-12-5.mol

Synonyms:methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside

There total 4 articles about methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-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: 93.0%

ethyl 3-O-[3-(methyl 2,3-di-O-benzyl-α-D-glucopyranoside-6-yloxymethyl)-benzyl]-2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (241471-11-4) → methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside (241471-12-5)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; for 0.5h;

DOI:10.1021/jo990132e

Reference yield:

ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (174172-99-7) → methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside (241471-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 54 percent / sodium hydride / dimethylformamide / 2 h / 0 °C

2.1: dibutyltin oxide / toluene / 4 h / Heating

2.2: 65 percent / tetrabutylammonium bromide / toluene / 20 h / 90 °C

3.1: 93 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂ / 0.5 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydride; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Alkylation / 2.1: Substitution / 2.2: Alkylation / 3.1: Cyclization;

DOI:10.1021/jo990132e

Reference yield:

ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside (241471-10-3) → methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside (241471-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / toluene / 4 h / Heating

1.2: 65 percent / tetrabutylammonium bromide / toluene / 20 h / 90 °C

2.1: 93 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂ / 0.5 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; di(n-butyl)tin oxide; In dichloromethane; toluene; 1.1: Substitution / 1.2: Alkylation / 2.1: Cyclization;

DOI:10.1021/jo990132e

upstream raw materials:

ethyl 3-O-[3-(methyl 2,3-di-O-benzyl-α-D-glucopyranoside-6-yloxymethyl)-benzyl]-2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside

1,3-bis-(bromomethyl)benzene

Downstream raw materials:

methyl α-D-glucopyranosyl-(1->4)-α-D-glucopyranoside