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

Base Information

• Chemical Name: phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 1235579-84-6
• Molecular Formula: C₃₄H₃₄O₆S
• Molecular Weight: 570.706
• Mol file: 1235579-84-6.mol

Synonyms:phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-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: 94.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) + p-methoxybenzyl chloride (824-94-2) → phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (1235579-84-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/d0ob00240b

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (1235579-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / toluene / 3 h / 120 °C

1.2: 120 °C

2.1: sodium hydride / N,N-dimethyl-formamide

With sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene;

DOI:10.1039/d0ob00240b

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (1235579-84-6) → C56H60O12 + C56H60O12

Guidance literature:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; phenyl 2-O-(4-methoxybenzyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; In diethyl ether; dichloromethane; at -78 ℃; for 0.333333h; Inert atmosphere;

With trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -45 ℃; Inert atmosphere;

DOI:10.1016/j.carres.2012.12.015

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

p-methoxybenzyl chloride

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

1-O-(tert-butyldiphenylsilyl)-2-O-(2-O-(4-methoxybenzyl)-3-O benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol

C₈₃H₈₈O₁₇

C₈₃H₈₈O₁₇