3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside
• CAS No.: 1361996-92-0
• Molecular Formula: C₅₁H₆₄O₁₉S
• Molecular Weight: 1013.12

Synonyms:3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside

Chemical Property of 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside

There total 8 articles about 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-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: 69.0%

1,2,3-trimethoxybenzene (621-23-8) + pent-4-enyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside (1203559-04-9) + 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-S-oxide (1361996-85-1) → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside (1361996-92-0)

Guidance literature:

1,2,3-trimethoxybenzene; 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-S-oxide; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -60 - -10 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

pent-4-enyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside; In dichloromethane; at 20 ℃; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201101889

Reference yield:

2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside (1361996-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.17 h / -60 - -10 °C / Inert atmosphere; Molecular sieve

3.2: 24 h / 20 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1002/chem.201101889

Reference yield:

2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (1197819-98-9) → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-pentenyl-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside (1361996-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylsilane; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / Inert atmosphere

2.1: pyridine / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.17 h / -60 - -10 °C / Inert atmosphere; Molecular sieve

4.2: 24 h / 20 °C / Inert atmosphere; Molecular sieve

With pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/chem.201101889

upstream raw materials:

C₁₄H₁₈O₆S

2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane

1,2,3-trimethoxybenzene

pent-4-enyl 2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranoside

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