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

Base Information

• Chemical Name: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside
• CAS No.: 1338548-66-5
• Molecular Formula: C₄₁H₄₄O₉S
• Molecular Weight: 712.861
• Mol file: 1338548-66-5.mol

Synonyms:phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside

Chemical Property of phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside

There total 1 articles about phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside 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: 86.0%

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-17-7) + phenyl 2,3-O-isopropylidene-1-thio-β-D-xylopyranoside (521304-46-1) → phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside (1338548-66-5)

Guidance literature:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -65 - -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With oct-1-ene; In dichloromethane; at -78 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

phenyl 2,3-O-isopropylidene-1-thio-β-D-xylopyranoside; In dichloromethane; at -60 ℃; for 2.5h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/jo201780e

Reference yield: 87.0%

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside (1338548-66-5) + benzoyl chloride (98-88-4) → phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside (1338548-68-7)

Guidance literature:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside; With acetic acid; at 65 ℃; for 3h;

benzoyl chloride; With pyridine; at 0 ℃; for 2h;

DOI:10.1021/jo201780e

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside (1338548-66-5) + benzoyl chloride (98-88-4) → phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside (1338548-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 3 h / 65 °C

1.2: 2 h / 0 °C

2.1: sodium cyanoborohydride / tetrahydrofuran / 1 h / 0 °C / Molecular sieve

With sodium cyanoborohydride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo201780e

upstream raw materials:

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

phenyl 2,3-O-isopropylidene-1-thio-β-D-xylopyranoside

Downstream raw materials:

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

phenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside