(4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne

Base Information

• Chemical Name: (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne
• CAS No.: 1158990-68-1
• Molecular Formula: C₂₁H₂₆O₂Si
• Molecular Weight: 338.522
• Mol file: 1158990-68-1.mol

Synonyms:(4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne

Chemical Property of (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne

There total 4 articles about (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne 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: 98.0%

(4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne (1158990-34-1) → (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne (1158990-68-1)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃; for 3h;

DOI:10.1039/c2ob25766a

Reference yield:

(R)-(tert-butyldiphenylsilyloxy)methyloxirane (107033-46-5) → (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne (1158990-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: 1.33 h / -78 - 0 °C / Inert atmosphere

2.1: methanol; potassium carbonate / 3 h / 20 °C

With methanol; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; hexane;

DOI:10.1039/c2ob25766a

Reference yield:

tert-butyldiphenylsilyl triflate (92886-86-7) → (4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne (1158990-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 20 °C

2.1: tert.-butyl lithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 1.33 h / -78 - 0 °C / Inert atmosphere

3.1: methanol; potassium carbonate / 3 h / 20 °C

With 1H-imidazole; methanol; dmap; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1039/c2ob25766a

upstream raw materials:

(4R)-5-tert-butyldiphenylsilanyloxy-4-hydroxy-1-trimethylsilylpentyne

tert-butyldiphenylsilyl triflate

(R)-(tert-butyldiphenylsilyloxy)methyloxirane

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

(2S,6R)-7-(tert-butyldiphenylsilanyloxy)-1-((2R,4R,6R)-4-(tert-butyldiphenylsilanyloxy)-6-(2-(chloromethyl)oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-4-methylene-6-(triethylsilanyloxy)heptan-2-ol

(4R)-2-bromo-4-hydroxy-5-tert-butyldiphenylsilanyloxypentene

(4R)-2-bromo-4-triethylsilanyloxy-5-tert-butyldiphenylsilanyloxy-1-pentene