(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

Base Information

Chemical Name:(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne
CAS No.:562835-10-3
Molecular Formula:C₃₄H₄₆O₃Si₂
Molecular Weight:558.908
Hs Code.:

Synonyms:(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

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Chemical Property of (3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

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Technology Process of (3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

There total 6 articles about (3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne 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: 72.0%

: 3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde

: 18107-18-1
diazomethyl-trimethyl-silane

: 562835-10-3
(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

Guidance literature:: diazomethyl-trimethyl-silane; With n-butyllithium; In hexane; at -78 ℃; for 0.5h;

3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-butyraldehyde; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h;
DOI:10.1021/jo050822k

Reference yield:

: C₃₄H₄₆Br₂O₃Si₂

: 562835-10-3
(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;
DOI:10.1021/ol0300569

Reference yield:

: (2S,3S)-3-benzyloxy-4-[tert-butyl(dimethyl)silyloxy]butane-1,2-diol

: 562835-10-3
(3S,4S)-4-benzyloxy-5-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)pent-1-yne

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 19 h / -78 °C

2.1: imidazole / dimethylformamide / 42 h / 50 °C

3.1: 3.94 g / EtMgBr / diethyl ether / 22 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5.1: nBuLi / hexane / 0.5 h / -78 °C

5.2: 72 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

With 1H-imidazole; dmap; n-butyllithium; ethylmagnesium bromide; Dess-Martin periodane; triethylamine; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1021/jo050822k