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

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->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS No.: 1361996-87-3
• Molecular Formula: C₄₁H₅₄O₁₇S
• Molecular Weight: 850.936

Synonyms:

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

Chemical Property:

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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->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

There total 10 articles about 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 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:

1,2,3-trimethoxybenzene (621-23-8) + 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) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose + 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1361996-87-3)

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;

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose; In dichloromethane; at 20 ℃; for 18h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;

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 (RS)-S-oxide (1372765-79-1) → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1361996-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / -10 °C / Molecular sieve; Inert atmosphere

2: dichloromethane / 16 h / -40 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane;

DOI:10.1021/ja3018187

Reference yield:

1,2,3-trimethoxybenzene (621-23-8) → 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1361996-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / -10 °C / Molecular sieve; Inert atmosphere

2: dichloromethane / 16 h / -40 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane;

DOI:10.1021/ja3018187

upstream raw materials:

C₁₄H₁₈O₆S

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

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

1,2,3-trimethoxybenzene

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