(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran
CAS No.:400736-44-9
Molecular Formula:C₂₅H₄₆O₅SSi₂
Molecular Weight:514.874
Hs Code.:

Synonyms:(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

There total 10 articles about (2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran 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%

: 400737-73-7
(2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran

: 400736-44-9
(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 5h;
DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 400736-44-9
(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 1 h / 25 °C

1.2: dimethylformamide / 1.5 h / 25 °C

2.1: 4.06 g / ethylene glycol; p-toluenesulfonic acid / methanol / 12 h / 25 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h / -78 °C

5.1: 3 g / NaBH₄ / methanol / 0.08 h / 0 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

7.1: 67 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 5 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; ethylene glycol; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation;
DOI:10.1021/ja0304953

Reference yield:

: 327603-45-2
phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside

: 400736-44-9
(2S,3S,4R,5S,6S)-2-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

2: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h / -78 °C

3: 3 g / NaBH₄ / methanol / 0.08 h / 0 °C

4: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

5: 67 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 5 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 2: Swern oxidation;
DOI:10.1021/ja0304953