phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside
• CAS No.: 819798-47-5
• Molecular Formula: C₄₁H₄₂O₆S
• Molecular Weight: 662.847
• Mol file: 819798-47-5.mol

Synonyms:phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-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%

benzyl bromide (100-39-0) + phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (179072-63-0) → phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (819798-47-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

DOI:10.1016/0040-4039(96)00901-X

Reference yield: 82.0%

phenyl 3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (819798-46-4) + benzyl bromide (100-39-0) → phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (819798-47-5)

Guidance literature:

phenyl 3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide;

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (819798-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO; 2.) CsF / 1.) MeOH, reflux, 2 h; 2.) DMF, 50 deg C, 2 d

2: 94 percent / NaH / dimethylformamide / 0.33 h / 0 °C

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

DOI:10.1016/0040-4039(96)00901-X

upstream raw materials:

benzyl bromide

phenyl 3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

p-methoxybenzyl chloride

Downstream raw materials:

phenyl 2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

C₆₈H₇₉NO₂₀

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

phenyl 2,4,6-tri-O-benzyl-3-O-chloroacetyl-1-thio-β-D-galactopyranoside