Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide

Base Information

• Chemical Name: Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide
• CAS No.: 188357-34-8
• Molecular Formula: C₂₉H₃₂O₆S
• Molecular Weight: 508.635
• Mol file: 188357-34-8.mol

Synonyms:Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide

Chemical Property of Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide

Chemical Property:

• Melting Point: 123-124°C
• Refractive Index: 1.63
• PSA: 82.43000
• LogP: 6.10500
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranoside S-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used in direct synthesis of β-mannopyranosides by the sulfoxide method. Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide can be used in direct synthesis of β-mannopyranosides by the sulfoxide method.

Technology Process of Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide

There total 10 articles about Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide 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: 83.0%

ethyl 4,6-O-benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside S-oxide (188357-34-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.8b00413

Reference yield: 80.0%

benzyl chloride (100-44-7) + S-ethyl 4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside (153062-17-0) → ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside S-oxide (188357-34-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 120 ℃; for 3h;

DOI:10.1016/S0040-4020(98)00426-8

Reference yield: 35.0%

benzyl bromide (100-39-0) + S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (R)S-oxide → (2R,4aR,6R,7S,8S,8aR)-7,8-Bis-benzyloxy-6-((R)-ethanesulfinyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (220155-65-7,188357-34-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1039/a804126a

upstream raw materials:

benzyl bromide

ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

benzyl chloride

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