(S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

Base Information

• Chemical Name: (S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester
• CAS No.: 179943-74-9
• Molecular Formula: C₁₅H₂₀O₃Si
• Molecular Weight: 276.408
• Mol file: 179943-74-9.mol

Synonyms:(S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

Chemical Property of (S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of (S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

There total 1 articles about (S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester 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:

(S)-(-)-glycidate de benzyle (110994-90-6) + trimethylsilylacetylene (1066-54-2) → (S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester (179943-74-9)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction;

DOI:10.1021/ja9607796

Reference yield: 72.0%

(S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester (179943-74-9) + methyl iodide (74-88-4) → (S)-2-Methoxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester (179943-90-9)

Guidance literature:

With silver(l) oxide; In dichloromethane; at 50 ℃; for 24h;

DOI:10.1021/ja9607796

Reference yield:

(S)-2-Hydroxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester (179943-74-9) → (4E,6Z)-(S)-6-Bromo-7-{(4S,5R)-5-[(E)-(1R,7R,8S,9R)-9-(tert-butyl-diphenyl-silanyloxy)-2,8-dihydroxy-1,5,7-trimethyl-4-oxo-dec-5-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxy-hepta-4,6-dienoic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / Ag₂O / CH₂Cl₂ / 24 h / 50 °C

2: 81 percent / aq. KF / dimethylformamide / 20 h

3: 1.) catecholborane, 2.) H₂O, 3.) TlOH, Pd₂(dba)3, Ph₃P

4: HF / acetonitrile

With potassium fluoride; TlOH; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen fluoride; water; triphenylphosphine; silver(l) oxide; benzo[1,3,2]dioxaborole; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja9607796

upstream raw materials:

(S)-(-)-glycidate de benzyle

trimethylsilylacetylene

Downstream raw materials:

(S)-2-Methoxy-5-trimethylsilanyl-pent-4-ynoic acid benzyl ester

benzyl(2S)-2-methoxy-4-pentynoate