phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

Base Information

• Chemical Name: phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
• CAS No.: 190443-02-8
• Molecular Formula: C₃₄H₃₆O₅S
• Molecular Weight: 556.723
• Mol file: 190443-02-8.mol

Synonyms:phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

Chemical Property of phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

There total 3 articles about phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 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:

p-methoxybenzyl chloride (824-94-2) → phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (190443-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) tetra n-butyl ammonium iodide / 1) CH₃OH, reflux, 24 h; 2) THF, reflux, 24 h

2: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, 2 h

With tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide;

DOI:10.1080/07328309808002905

Reference yield:

phenyl 6-deoxy-1-thio-β-L-galactopyranoside (187233-24-5) → phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (190443-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) tetra n-butyl ammonium iodide / 1) CH₃OH, reflux, 24 h; 2) THF, reflux, 24 h

2: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, 2 h

With tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide;

DOI:10.1080/07328309808002905

Reference yield:

benzyl bromide (100-39-0) + phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (208661-98-7) → phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (190443-02-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) DMF, 0 deg C, 30 min; 2) DMF, 2 h;

DOI:10.1080/07328309808002905

upstream raw materials:

benzyl bromide

phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

p-methoxybenzyl chloride

phenyl 6-deoxy-1-thio-β-L-galactopyranoside

Downstream raw materials:

(4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

(4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol