Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
CAS No.:847944-57-4
Molecular Formula:C₂₆H₃₈O₇S₂Si
Molecular Weight:554.801
Hs Code.:

Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Synonyms:Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 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: 87.0%

: 795289-94-0
4-O-tert-butyldimethylsilyl-3-O-methyl-6-O-tosyl-D-glucal

: 108-98-5
thiophenol

: 847944-57-4
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: 4-O-tert-butyldimethylsilyl-3-O-methyl-6-O-tosyl-D-glucal; thiophenol; With N-chloro-succinimide; In dichloromethane; at 20 ℃; for 1h;

With silver carbonate; In water; acetonitrile; at 20 ℃; for 14h;
DOI:10.1002/chem.200600462

Reference yield:

: 795289-93-9
4,6-O-(di-tert-butyl)-silyliden-3-O-methyl-D-glucal

: 847944-57-4
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

2.1: 94 percent / pyridine / CH₂Cl₂ / 14 h / 20 °C

3.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -60 °C

4.1: NCS / CH₂Cl₂ / 1 h / 20 °C

4.2: 87 percent / Ag₂CO₃ / acetonitrile; H₂O / 14 h / 20 °C

With pyridine; 2,6-dimethylpyridine; N-chloro-succinimide; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200600462

Reference yield:

: 916221-16-4
Toluene-4-sulfonic acid (2R,3S,4R)-3-hydroxy-4-methoxy-3,4-dihydro-2H-pyran-2-ylmethyl ester

: 847944-57-4
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4-methoxy-5-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -60 °C

2.1: NCS / CH₂Cl₂ / 1 h / 20 °C

2.2: 87 percent / Ag₂CO₃ / acetonitrile; H₂O / 14 h / 20 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; In dichloromethane;
DOI:10.1002/chem.200600462