(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

Base Information

Chemical Name:(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine
CAS No.:406220-30-2
Molecular Formula:C₂₉H₃₉NO₅Si
Molecular Weight:509.718
Hs Code.:

Synonyms:(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

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Chemical Property of (2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

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Technology Process of (2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

There total 6 articles about (2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine 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: 68.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 150943-17-2
(2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone

: 406220-30-2
(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; Inert atmosphere;

(2R)-1-(tert-butyloxycarbonyl)-2-((tert-butyldiphenylsilyl)oxymethyl)-3-azetidinone; In tetrahydrofuran; mineral oil; at -78 - 20 ℃; for 2.75h; Inert atmosphere;
DOI:10.3762/bjoc.10.110

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 406220-30-2
(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydroxide / 1,4-dioxane; water / 0 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: 4-methyl-morpholine / dichloromethane / 1 h / -5 °C / Inert atmosphere

4.1: acetonitrile; hexane / 43 h / 4 °C / Inert atmosphere

5.1: dirhodium tetraacetate / dichloromethane / -95 - 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

6.2: 2.75 h / -78 - 20 °C / Inert atmosphere

With 4-methyl-morpholine; 1H-imidazole; dirhodium tetraacetate; sodium hydride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 6.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.3762/bjoc.10.110

Reference yield:

: C₂₇H₃₇NO₇Si

: 406220-30-2
(2S,E)-1-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-ethoxy-2-oxoethylidene)azetidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetonitrile; hexane / 43 h / 4 °C / Inert atmosphere

2.1: dirhodium tetraacetate / dichloromethane / -95 - 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

3.2: 2.75 h / -78 - 20 °C / Inert atmosphere

With dirhodium tetraacetate; sodium hydride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; mineral oil; 3.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.3762/bjoc.10.110