2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-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)-S-oxide
CAS No.:1361996-85-1
Molecular Formula:C₂₀H₂₄O₉S
Molecular Weight:440.471
Hs Code.:

Synonyms: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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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)-S-oxide

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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)-S-oxide

There total 8 articles about 2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (S)-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: 80.0%

: (2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine

: 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)-S-oxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.416667h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201101889

Reference yield:

: (2S,4aS,6R,7R,8S,8aR)-6-acetoxymethyl-7,8-diacetoxy-2-phenylhexahydro-4aH-pyrano[3,2-b][1,4]oxathiine

: 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)-S-oxide

: 1379827-81-2
2-(S)-phenyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane-S-oxide

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; 1,1'-sulfinylbisbenzene; In dichloromethane; at -60 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

With methanol; In dichloromethane; at -60 - 20 ℃; for 1.5h; optical yield given as %de; Inert atmosphere; Molecular sieve;
DOI:10.1002/chem.201102861

Reference yield:

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

: 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)-S-oxide

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere

With pyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1002/chem.201101889