phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 146820-14-6
• Molecular Formula: C₄₀H₃₈O₆S
• Molecular Weight: 646.804
• Mol file: 146820-14-6.mol

Synonyms:phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 9 articles about phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-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: 70.0%

C37H40O5 + thiophenol (108-98-5) → phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (146820-14-6)

Guidance literature:

In 1,2-dichloro-ethane; at 24 ℃; Reflux; Inert atmosphere;

DOI:10.1002/chem.201304950

Reference yield:

benzoyl chloride (98-88-4) + (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (354114-14-0) → phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (146820-14-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 2 ℃; for 18h; Inert atmosphere;

DOI:10.1039/c7ob02968c

Reference yield:

Acetic acid (3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester → phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (146820-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol / 18 h / pH 10 / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 18 h / 2 °C / Inert atmosphere

With dmap; sodium methylate; triethylamine; In methanol; dichloromethane;

DOI:10.1039/c7ob02968c

upstream raw materials:

benzoyl chloride

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

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose

thiophenol

Downstream raw materials:

Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(8-methoxycarbonyl-octyloxy)-tetrahydro-pyran-3-yl ester

8-methoxycarbonyloctyl (2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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

2-O-benzoyl-3,4,6-tetra-O-benzyl-α-D-mannopyranoside