(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

Base Information

Chemical Name:(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one
CAS No.:1351186-11-2
Molecular Formula:C₃₂H₃₇NO₄Si
Molecular Weight:527.736
Hs Code.:

Synonyms:(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

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Chemical Property of (R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

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Technology Process of (R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

There total 1 articles about (R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one 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: 50.0%

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 227602-33-7
diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate

: 1351186-11-2
(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

Guidance literature:: diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/jo201951s

Reference yield:

: 1351186-11-2
(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

: 75-16-1
methylmagnesium bromide

: 1351186-13-4
(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

: (R)-3-((3R,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

Guidance literature:: methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one; In tetrahydrofuran; at -78 - -40 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo201951s

Reference yield:

: 1351186-11-2
(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

: 320742-77-6
(R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: -78 - -40 °C / Inert atmosphere

2.1: lithium borohydride / methanol / 0.5 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 - 40 °C

5.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

6.1: diethyl cyanophosphonate; triethylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

With lithium borohydride; sodium azide; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Staudinger reaction;
DOI:10.1021/jo201951s