phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide

Base Information

• Chemical Name: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide
• CAS No.: 157087-54-2
• Molecular Formula: C₄₀H₄₀O₆S
• Molecular Weight: 648.82
• Mol file: 157087-54-2.mol

Synonyms:phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide

Chemical Property of phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide

There total 3 articles about phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide 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:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside sulfoxide (117307-17-2) + phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide (157087-54-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1002/jlac.199719970910

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide (157087-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.4 percent / NaH / dimethylsulfoxide / 3 h / 20 °C

2: m-chloroperbenzoic acid / CH₂Cl₂ / -78 - 0 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; 1: Etherification / 2: Oxidation;

Reference yield:

benzyl bromide (100-39-0) → phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide (157087-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.4 percent / NaH / dimethylsulfoxide / 3 h / 20 °C

2: m-chloroperbenzoic acid / CH₂Cl₂ / -78 - 0 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; 1: Etherification / 2: Oxidation;

upstream raw materials:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

benzyl bromide

Downstream raw materials:

methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3,4,6-O-benzyl-α-D-glucopyranosyl]-(1->4)-α-D-glucopyranoside