phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 158198-56-2
• Molecular Formula: C₂₈H₂₈O₆S
• Molecular Weight: 492.593
• Mol file: 158198-56-2.mol

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

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

There total 8 articles about phenyl 2-O-acetyl-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: 93.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) + acetic anhydride (108-24-7) → phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (158198-56-2)

Guidance literature:

With pyridine; In dichloromethane; for 5h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00218-3

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-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (158198-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium hydride, 2.) cupric chloride / 1.) Me₂NCHO, RT, 2) Me₂NCHO, 4 h, 70 deg C

2: 93 percent / pyridine / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; sodium hydride; copper dichloride; In dichloromethane;

DOI:10.1016/S0008-6215(98)00218-3

Reference yield:

phenyl 2,3,4,6-tetra-O-trimethylsilyl-1-thio-β-D-glucopyranoside (128848-50-0) → C24H26O7S + phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (158198-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylsilane; iron (III) chloride hexahydrate / dichloromethane; acetonitrile / 0 - 20 °C

2: water / 12 h / 20 °C

With triethylsilane; iron (III) chloride hexahydrate; In dichloromethane; water; acetonitrile;

DOI:10.1039/c0cc04398b

upstream raw materials:

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

acetic anhydride

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

benzyl bromide

Downstream raw materials:

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

phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

C₇₃H₇₈N₂O₁₇S