S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

Base Information

• Chemical Name: S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside
• CAS No.: 403646-50-4
• Molecular Formula: C₃₅H₃₆O₇S
• Molecular Weight: 600.733
• Mol file: 403646-50-4.mol

Synonyms:S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

Chemical Property of S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

There total 5 articles about S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside 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: 95.0%

p-methoxybenzyl chloride (824-94-2) + phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside (403646-50-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside (403646-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

2: sodium hydride / N,N-dimethyl-formamide / 20 °C

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

Reference yield:

thiophenol (108-98-5) → S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside (403646-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / 40 h / 22 °C / Large scale

2: sodium methylate / methanol / 22 °C / Large scale

3: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

4: sodium hydride / N,N-dimethyl-formamide / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

p-methoxybenzyl chloride

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

per-O-acetyl-α-D-mannopyranose

thiophenol

Downstream raw materials:

2-azidoethyl 2,3-di-O-(p-methoxybenzyl)-4,6-O-benzylidene-β-D-mannopyranoside

2-azidoethyl 2,3-di-O-(p-methoxybenzyl)-4,6-O-benzylidene-α-D-mannopyranoside

phenyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-α-D-mannopyranoside

2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside