(S)-4-trimethylsilyl-3-butyn-2-ol

Base Information

• Chemical Name: (S)-4-trimethylsilyl-3-butyn-2-ol
• CAS No.: 103253-60-7
• Molecular Formula: C₇H₁₄OSi
• Molecular Weight: 142.273
• Mol file: 103253-60-7.mol

Synonyms:

Chemical Property of (S)-4-trimethylsilyl-3-butyn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: (S)-4-Trimethylsilyl-3-butyn-2-ol (also referred to as (S)-TMSBL) is a chiral propargylic alcohol that serves as a key intermediate in the synthesis of biologically active compounds and pharmaceuticals. It can be obtained enantioselectively through light-controlled asymmetric hydrogenation of 4-(trimethylsilyl)-3-butyn-2-one (TMSBO) using photosynthetic bacteria *Rhodobacter sphaeroides*, which harnesses light energy for NADPH generation without requiring oxygen. Optimized conditions for its production include specific parameters such as pH, temperature, and substrate concentration, enhancing yield efficiency. Additionally, selective deprotection methods for silylated alkynols, including (S)-TMSBL, have been developed, improving synthetic accessibility. Its structural features make it valuable in stereocontrolled organic synthesis, as demonstrated in the preparation of complex intermediates like those used in epolactaene synthesis. **Other names for (S)-4-trimethylsilyl-3-butyn-2-ol:** - (S)-TMSBL - (S)-4-(Trimethylsilyl)-3-butyn-2-ol

Technology Process of (S)-4-trimethylsilyl-3-butyn-2-ol

There total 31 articles about (S)-4-trimethylsilyl-3-butyn-2-ol 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: 99.0%

4-trimethylsilyl-3-butyn-2-one (5930-98-3) → (S)-4-trimethylsilyl-3-butyn-2-ol (6999-19-5,103253-60-7,121522-26-7,121522-27-8)

Guidance literature:

With potassium hydroxide; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide; In isopropyl alcohol; at 28 ℃; for 12h;

DOI:10.1021/ja971570a

Reference yield: 95.0%

chloro-trimethyl-silane (75-77-4) + but-3-yn-2-ol (2028-63-9) → 4-trimethylsilyl-3-butyn-2-ol (103253-60-7,121522-26-7,121522-27-8,6999-19-5)

Guidance literature:

but-3-yn-2-ol; With ethylmagnesium bromide; In tetrahydrofuran;

chloro-trimethyl-silane; In tetrahydrofuran; for 2h; Heating;

DOI:10.1002/hlca.200290002

Reference yield: 94.0%

ethylmagnesium bromide (925-90-6) + but-3-yn-2-ol (2028-63-9) → 4-trimethylsilyl-3-butyn-2-ol (103253-60-7,121522-26-7,121522-27-8,6999-19-5)

Guidance literature:

With hydrogenchloride; chloro-trimethyl-silane; In tetrahydrofuran;

upstream raw materials:

methyl magnesium iodide

3-(trimethylsilyl)prop-2-yn-1-al

chloro-trimethyl-silane

but-3-yn-2-ol

Downstream raw materials:

(R)-4-trimethylsilyl-3-butyn-2-yl acetate

(S)-4-trimethylsilyl-3-butyn-2-ol

5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate

4-(4-methoxyphenyl)but-3-yn-2-ol