methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide

Base Information

• Chemical Name: methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide
• CAS No.: 149440-84-6
• Molecular Formula: C₃₅H₃₈O₅S₂
• Molecular Weight: 602.816
• Mol file: 149440-84-6.mol

Synonyms:

Chemical Property of methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide

There total 2 articles about methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide 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:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide (149440-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) P(Et₂N)3, CCl₄ / 1) CH₂Cl₂, -40 deg C, 30 min, 2) -40 deg C, 2 h

2: 1) NaOEt / 1) THF, r.t., 30 min, 2) THF, r.t., 2 h

With tetrachloromethane; sodium ethanolate; hexaethylphosphoric triamide;

DOI:10.1002/hlca.19930760223

Reference yield:

dimethyl(methylthio)sulfonium tetrafluoroborate (5799-67-7) + O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl) dithiocarbonate (116429-59-5) → methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide (149440-84-6)

Guidance literature:

With sodium ethanolate; Yield given. Multistep reaction; 1) THF, r.t., 30 min, 2) THF, r.t., 2 h;

DOI:10.1002/hlca.19930760223

Reference yield:

methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl disulfide (149440-84-6) → 2,3,4,6-tetra-O-benzyl-1-thio-D-mannono-1,5-O-lactone (149561-02-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction; 1) CH₂Cl₂, 0 deg C, 1 h, 2) 120 deg C / 0.05 mbar, 15 min;

DOI:10.1002/hlca.19930760223

upstream raw materials:

dimethyl(methylthio)sulfonium tetrafluoroborate

O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl) dithiocarbonate

2,3,4,6-tetra-O-benzyl-D-mannopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-1-thio-D-mannono-1,5-O-lactone