3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
CAS No.:1361996-93-1
Molecular Formula:C₄₁H₅₄O₁₇S
Molecular Weight:850.936
Hs Code.:

Synonyms:3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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Chemical Property of 3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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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->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 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: 82.0%

: 621-23-8
1,2,3-trimethoxybenzene

: 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

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 1361996-93-1
3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; In dichloromethane; at -10 - 20 ℃; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1002/chem.201101889

Reference yield:

: 1197819-96-7
C₁₄H₁₈O₆S

: 1361996-93-1
3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / Inert atmosphere

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

3.1: pyridine / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.42 h / -78 °C / Inert atmosphere

5.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.17 h / -60 - -10 °C / Inert atmosphere; Molecular sieve

5.2: 24 h / -10 - 20 °C / Inert atmosphere; Molecular sieve

With pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1002/chem.201101889

Reference yield:

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

: 1361996-93-1
3,4,6-tri-O-acetyl-2-O-[1-(S)-phenyl-2-(2,4,6-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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 / -10 - 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