tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

Base Information

Chemical Name:tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate
CAS No.:906528-71-0
Molecular Formula:C₂₆H₃₅NO₄Si
Molecular Weight:453.654
Hs Code.:

Synonyms:tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

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Technology Process of tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

There total 4 articles about tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate 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: 89.0%

: 906528-70-9
tert-butyl (2R,3R)-1,3-dihydroxypent-4-yn-2-ylcarbamate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 906528-71-0
tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.bmc.2006.03.048

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 906528-71-0
tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi; ZnBr₂ / diethyl ether; hexane / 0 - 20 °C

1.2: 41 percent / diethyl ether; hexane / -78 - 20 °C

2.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3.1: 93 percent / acetic acid / 5 h / 60 °C

4.1: 89 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; tetrabutyl ammonium fluoride; acetic acid; zinc dibromide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.03.048

Reference yield:

: 129786-70-5
(4R)-4-((1R)-1-hydroxy-3-trimethylsilanyl-prop-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 906528-71-0
tert-butyl (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-hydroxypent-4-yn-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: 93 percent / acetic acid / 5 h / 60 °C

3: 89 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.03.048