(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate
• CAS No.: 591770-18-2
• Molecular Formula: C₂₅H₄₈O₅SSi₂
• Molecular Weight: 516.89
• Mol file: 591770-18-2.mol

Synonyms:(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate

Chemical Property of (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate

There total 8 articles about (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentan-1-ol (591770-17-1) → (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate (591770-18-2)

Guidance literature:

With pyridine; at 23 ℃; for 2h;

DOI:10.1055/s-2003-40210

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate (591770-18-2)

Guidance literature:

Multi-step reaction with 4 steps

1: TiCl₄; sparteine / CH₂Cl₂ / 0 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 23 °C

3: 75 percent / aq. NaBH₄ / tetrahydrofuran / 2 h / 23 °C

4: 95 percent / pyridine / 2 h / 23 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; titanium tetrachloride; (-)-sparteine; In tetrahydrofuran; dichloromethane; 1: Evans aldol reaction;

DOI:10.1055/s-2003-40210

Reference yield:

(4R)-4-benzyl-3-[(2R,3S)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-15-9) → (2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl 4-methylbenzenesulfonate (591770-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 23 °C

2: 75 percent / aq. NaBH₄ / tetrahydrofuran / 2 h / 23 °C

3: 95 percent / pyridine / 2 h / 23 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2003-40210

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentan-1-ol

t-butyldimethylsiyl triflate

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfonyl}-1-phenyl-1H-tetrazole

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

{(1E,3R,4S)-4,6-bis{[(tert-butyl)dimethylsilyl]oxy}-3-methylhex-1-enyl}benzene

(3S,4R,5E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-6-phenylhex-5-en-1-ol