phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 158716-07-5
• Molecular Formula: C₂₆H₂₆O₅S
• Molecular Weight: 450.555
• Mol file: 158716-07-5.mol

Synonyms:phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

• Melting Point: 89-94 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: This is a protected mannopyranoside useful as a building block for synthesis of complex carbohydrates. The compound has α-phenylthio, 3-benzyl and 4,6-benzylidene protecting groups.

Technology Process of phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 14 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 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: 96.0%

benzyl bromide (100-39-0) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (158716-07-5)

Guidance literature:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; at 110 ℃;

benzyl bromide; With tetrabutylammomium bromide; In toluene; at 80 ℃;

Reference yield: 89.0%

C27H36O5SSn + benzyl bromide (100-39-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (158716-07-5)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jacs.5b06126

Reference yield: 73.7%

phenyl exo(phenyl)-2,3:4,6-di-O-benzylidene-1-thio-α-D-mannopyranoside (158716-04-2) → phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside (158716-08-6) + phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (158716-07-5)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane; for 0.75h;

DOI:10.1016/0008-6215(94)84264-7

upstream raw materials:

phenyl exo(phenyl)-2,3:4,6-di-O-benzylidene-1-thio-α-D-mannopyranoside

benzyl bromide

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

((2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tert-butyl-dimethyl-silane

phenyl 4,6-O-benzylidene-2-O-(3-naphthalen-1-yl-prop-2-ynyl)-3-O-benzyl-1-thio-α-D-mannopyranoside

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

phenyl 3-O-benzyl-4,6-O-benzylidene-3-2-O-(2,2-dimethyltrimethylene phosphornoyl)-α-D-thiomannopyranoside