(2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol

Base Information

• Chemical Name: (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol
• CAS No.: 922493-40-1
• Molecular Formula: C₂₉H₃₈O₃Si
• Molecular Weight: 462.704
• Mol file: 922493-40-1.mol

Synonyms:(2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol

Chemical Property of (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol

There total 6 articles about (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol 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: 90.0%

(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol (73814-98-9,73814-99-0,105560-79-0,143005-16-7) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol (922493-40-1)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/anie.200602033

Reference yield:

(3S,4R)-1-Benzyloxy-4-methyl-hex-5-en-3-ol (909803-71-0) → (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol (922493-40-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.07 g / pyridine / CH₂Cl₂

2.1: O₃; O₂ / CH₂Cl₂ / -78 °C

2.2: triphenylphosphine / CH₂Cl₂ / 20 °C

3.1: NaBH₄ / ethanol / 0.5 h

3.2: 382 mg / K₂CO₃ / methanol / 24 h / 20 °C

4.1: 90 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; oxygen; ozone; In ethanol; dichloromethane;

DOI:10.1002/anie.200602033

Reference yield:

C15H20O4 → (2R,3S)-1-[(tert-butyldiphenylsilyl)oxy]-5-benzyloxy-2-methyl-3-pentanol (922493-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaBH₄ / ethanol / 0.5 h

1.2: 382 mg / K₂CO₃ / methanol / 24 h / 20 °C

2.1: 90 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; In ethanol; dichloromethane;

DOI:10.1002/anie.200602033

upstream raw materials:

(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol

tert-butylchlorodiphenylsilane

(3S,4R)-1-Benzyloxy-4-methyl-hex-5-en-3-ol

C₁₆H₂₂O₃

Downstream raw materials:

C₂₉H₃₇O₂SiN₃

C₃₃H₄₉NO₅Si

C₃₁H₄₅NO₅Si

C₃₁H₄₆N₂O₄Si