2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide

Base Information

• Chemical Name: 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide
• CAS No.: 1379827-90-3
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 442.472

Synonyms:2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide

Chemical Property of 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide

Chemical Property:

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Technology Process of 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide

There total 3 articles about 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide 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%

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) → 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S(18)O-oxide + 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide (1379827-90-3)

Guidance literature:

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; <18O>diphenyl sulfoxide; In dichloromethane; at -60 ℃; for 0.666667h; Inert atmosphere;

With diphenyl sulfide; In dichloromethane; at -60 - 20 ℃; for 0.166667h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/chem.201102861

Reference yield: 69.0%

(2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine → 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide (1379827-90-3)

Guidance literature:

(2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; <18O>diphenyl sulfoxide; In dichloromethane; at -60 - -30 ℃; for 1.16667h; Molecular sieve; Inert atmosphere;

With methanol; In dichloromethane; at -60 - 20 ℃; for 1.5h; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201102861

Reference yield:

(2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine → 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S(18)O-oxide + 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide (1379827-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 0.08 h / -60 °C / Molecular sieve; Inert atmosphere

1.2: 1.5 h / -60 - 20 °C / Inert atmosphere; Molecular sieve

2.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; <18O>diphenyl sulfoxide / dichloromethane / 0.67 h / -60 °C / Inert atmosphere

2.2: 0.17 h / -60 - 20 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; <18O>diphenyl sulfoxide; In dichloromethane;

DOI:10.1002/chem.201102861

upstream raw materials:

2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-S-oxide

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