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

Base Information

• Chemical Name: 2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane
• CAS No.: 1197819-98-9
• Molecular Formula: C₁₅H₂₀O₆S
• Molecular Weight: 328.386

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

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

Chemical Property:

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

There total 4 articles about 2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane 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: 61.0%

methanol (67-56-1) + C14H18O6S (1197819-96-7) → 2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (1197819-98-9)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 28h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/b913308a

Reference yield:

β-D-glucose pentaacetate (604-69-3) → 2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (1197819-98-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate; thiourea / acetonitrile / Reflux; Inert atmosphere

1.2: Inert atmosphere

2.1: sodium methylate / methanol / Inert atmosphere

3.1: toluene-4-sulfonic acid / Inert atmosphere

With boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; thiourea; In methanol; acetonitrile;

DOI:10.1002/chem.201101889

Reference yield:

2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosyl acetophenone (3254-12-4) → 2-methoxy-2-(S)-phenyl-(1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (1197819-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol / Inert atmosphere

2: toluene-4-sulfonic acid / Inert atmosphere

With sodium methylate; toluene-4-sulfonic acid; In methanol;

DOI:10.1002/chem.201101889

upstream raw materials:

methanol

C₁₄H₁₈O₆S

2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosyl acetophenone

α-bromoacetophenone

Downstream raw materials:

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

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

3,4,6-tri-O-benzyl-2-O-[1-(S)-phenyl-2-(methylsulfanyl)ethyl]-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-D-galactopyranose

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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