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

Base Information

• Chemical Name: (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran
• CAS No.: 400737-73-7
• Molecular Formula: C₂₅H₄₆O₄SSi₂
• Molecular Weight: 498.875
• Mol file: 400737-73-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-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: 100.0%

t-butyldimethylsiyl triflate (69739-34-0) + phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside (400737-69-1) → (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (400737-73-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 1h;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (400737-73-7)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja0304953

Reference yield:

phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside (327603-45-2) → (2S,3S,4R,5S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran (400737-73-7)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 2: Swern oxidation;

DOI:10.1021/ja0304953

upstream raw materials:

t-butyldimethylsiyl triflate

phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

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