methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside
• CAS No.: 1338548-89-2
• Molecular Formula: C₅₃H₆₆O₂₇
• Molecular Weight: 1135.09

Synonyms:methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Chemical Property of methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Chemical Property:

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Safty Information:

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Technology Process of methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

There total 6 articles about methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-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: 85.0%

methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (1338548-88-1) + phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-1-thio-β-D-xylopyranoside (1338548-86-9) → methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (1338548-89-2)

Guidance literature:

phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-1-thio-β-D-xylopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; In dichloromethane; at -65 - -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside; In dichloromethane; at -70 - -60 ℃; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/jo201780e

Reference yield:

phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-β-D-xylopyranoside (1338548-84-7) → methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (1338548-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / 3 h / 65 °C

1.2: 2 h / 0 °C

2.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -65 - -60 °C / Molecular sieve; Inert atmosphere

2.2: -70 - -60 °C / Molecular sieve; Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; acetic acid; In dichloromethane;

DOI:10.1021/jo201780e

Reference yield:

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-β-D-xylopyranoside (1338548-85-8) → methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranosyl-(1->4)-6-O-benzyl-2,3-di-O-acetyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (1338548-89-2)

Guidance literature:

Multi-step reaction with 3 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

3.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -65 - -60 °C / Molecular sieve; Inert atmosphere

3.2: -70 - -60 °C / Molecular sieve; Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo201780e

upstream raw materials:

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

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->4)-2,3-O-isopropylidene-β-D-xylopyranoside

methyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

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

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