(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

Base Information

Chemical Name:(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate
CAS No.:327977-95-7
Molecular Formula:C₂₀H₃₂O₅SSi
Molecular Weight:412.623
Hs Code.:

Synonyms:(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

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Chemical Property of (1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

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Technology Process of (1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

There total 4 articles about (1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl 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: 63.0%

: 56069-39-7
diethyl phenylsulfonylmethylphosphonate

: 327977-92-4
(1S)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)prop-2-enyl acetate

: 327977-95-7
(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

Guidance literature:: (1S)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)prop-2-enyl acetate; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 20 ℃;

diethyl phenylsulfonylmethylphosphonate; With triethylamine; lithium bromide; In acetonitrile; at 20 ℃;
DOI:10.1055/s-2000-8732

Reference yield:

: 87184-81-4
4-(tert-butyldimethylsilanyloxy)butanal

: 327977-95-7
(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 0 - 20 °C

2.1: 41 percent / Lipase PS "Amano" / diisopropyl ether / 72 h / 40 °C

3.1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

3.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

3.3: 63 percent / LiBr; Et₃N / acetonitrile / 20 °C

With Lipase PS "Amano"; sodium hydrogencarbonate; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; di-isopropyl ether; 1.1: Grignard addition / 3.3: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-2000-8732

Reference yield:

: 87184-99-4
4-tert-butyldimethylsilyloxybutan-1-ol

: 327977-95-7
(1S,2E)-1-(3-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}propyl)-3-(phenylsulfonyl)prop-2-enyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Dess-Martin's periodinane / CH₂Cl₂ / 20 °C

2.1: tetrahydrofuran; diethyl ether / 0 - 20 °C

3.1: 41 percent / Lipase PS "Amano" / diisopropyl ether / 72 h / 40 °C

4.1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

4.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

4.3: 63 percent / LiBr; Et₃N / acetonitrile / 20 °C

With Lipase PS "Amano"; sodium hydrogencarbonate; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; di-isopropyl ether; 1.1: Dess-Martin oxidation / 2.1: Grignard addition / 4.3: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-2000-8732