(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

Base Information

Chemical Name:(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate
CAS No.:914248-39-8
Molecular Formula:C₃₀H₃₄O₄Si
Molecular Weight:486.683
Hs Code.:

Synonyms:(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

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Chemical Property of (1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

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Technology Process of (1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

There total 3 articles about (1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate 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: 95.0%

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 84681-19-6
(R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy

: 914248-39-8
(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

Guidance literature:: (R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy; With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 0.5h;

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal; In toluene; at 20 ℃; for 4h;
DOI:10.1021/ol0616539

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 84681-19-6
(R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy

: 914248-39-8
(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

: (1S,4S,5S)-5-tert-butyldiphenylsilyloxy-4-hydroxy-1-phenylhex-2-ynyl acetate

Guidance literature:: (R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy; With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 0.5h; Inert atmosphere;

(S)-2-(O-tert-butyldiphenylsilyloxy)propanal; In toluene; for 4h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jo8025753

Reference yield:

: 4187-87-5
1-Phenyl-2-propyn-1-ol

: 914248-39-8
(1S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-4-hydroxy-1-phenylhex-2-ynyl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Novozym 435 / 60 °C

2.1: zinc triflate; (-)-N-methylephedrine; Et₃N / toluene / 0.5 h / 20 °C

2.2: 95 percent / toluene / 4 h / 20 °C

With Novozym 435; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene;
DOI:10.1021/ol0616539