Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside

Base Information

• Chemical Name: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside
• CAS No.: 167612-35-3
• Molecular Formula: C33H34O4S
• Molecular Weight: 526.697
• Mol file: 167612-35-3.mol

Synonyms:Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside;Phenyl 2,3,4-Tri-O-benzyl-1-thio-β-L-fucopyranoside;Phenyl 2,3,4-Tri-O-benzyl-1-thio-&beta

Chemical Property of Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 106.0 to 110.0 °C
• Boiling Point: 644.498°C at 760 mmHg
• Flash Point: 343.58°C
• PSA: 62.22000
• Density: 1.205g/cm³
• LogP: 7.27970

Purity/Quality:

97% ^*data from raw suppliers

Phenyl 2,3,4-Tri-O-benzyl-1-thio-β-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside (CAS# 167612-35-3) is a useful carbohydrate used in the synthesis of asymmetric core-fucosylated and core-unmodified N-glycans.

Technology Process of Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside

There total 10 articles about Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-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: 90.0%

benzyl bromide (100-39-0) + phenyl 6-deoxy-1-thio-β-L-galactopyranoside (187233-24-5) → 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (167612-35-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo025579t

Reference yield:

benzyl chloride (100-44-7) + phenyl 6-deoxy-1-thio-β-L-galactopyranoside (187233-24-5) → 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (167612-35-3)

Guidance literature:

benzyl chloride; phenyl 6-deoxy-1-thio-β-L-galactopyranoside; With sodium hydroxide; In dichloromethane; for 1.5h; Reflux;

With methanol; In dichloromethane; Reflux;

Reference yield:

benzyl bromide (100-39-0) + phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside (127061-10-3) → 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (167612-35-3) + phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside (183875-25-4)

Guidance literature:

phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside; With sodium methylate; In methanol; for 0.166667h; Inert atmosphere;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.200704381

upstream raw materials:

benzyl bromide

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

thiophenol

phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside

Downstream raw materials:

(2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranosyl sulfoxide

2-{6-(2-azido-ethoxy)-8-[4,5-bis-benzyloxy-6-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-isoindole-1,3-dione

1-Benzyloxymethyl-9-[(2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one