(4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate

Base Information

• Chemical Name: (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate
• CAS No.: 251976-79-1
• Molecular Formula: C₂₃H₃₀O₄SSi
• Molecular Weight: 430.64
• Mol file: 251976-79-1.mol

Synonyms:(4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate

Chemical Property of (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate

There total 5 articles about (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate 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: 97.0%

methanesulfonyl chloride (124-63-0) + (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentyn-1-ol (251976-81-5) → (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate (251976-79-1)

Guidance literature:

With triethylamine; In dichloromethane; at -40 - 20 ℃;

DOI:10.1021/jo0200466

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methanesulfonyl chloride (124-63-0) + (S)-tert-butyl(4,4-dibromo-2-methylbut-3-en-1-yloxy)diphenylsilane (226079-85-2) → (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate (251976-79-1)

Guidance literature:

formaldehyd; (S)-tert-butyl(4,4-dibromo-2-methylbut-3-en-1-yloxy)diphenylsilane; With n-butyllithium;

methanesulfonyl chloride; With triethylamine;

DOI:10.1016/S0022-328X(02)01160-9

Reference yield:

(S)-tert-butyl(4,4-dibromo-2-methylbut-3-en-1-yloxy)diphenylsilane (226079-85-2) → (4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentynyl methanesulfonate (251976-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: BuLi / tetrahydrofuran / -78 - 0 °C

2: Et₃N / CH₂Cl₂ / -30 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane; 1: addition; dehydrobromination / 2: mesylation;

DOI:10.1021/ja991918x

upstream raw materials:

methanesulfonyl chloride

(4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-4-methyl-2-pentyn-1-ol

formaldehyd

(S)-tert-butyl(4,4-dibromo-2-methylbut-3-en-1-yloxy)diphenylsilane

Downstream raw materials:

tert-butyl (2S)-2-[(1S,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate

(2S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-2-(S)-pyrrolidin-2-yl-hept-4-yn-2-ol

(6Z,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydroindolizine

(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol