tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate
CAS No.:144564-16-9
Molecular Formula:C₂₉H₃₉NO₄Si
Molecular Weight:493.718
Hs Code.:

Synonyms:tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

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Technology Process of tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

There total 3 articles about tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate 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: 62.0%

: 138871-58-6
(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

: 1730-25-2
allylmagnesium bromide

: 144564-16-9
tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1021/jo701703e

Reference yield:

: 138629-30-8,138871-56-4
(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

: 144564-16-9
tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) hexamethyldisilazane, BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

2: 30percent H₂O₂ / ethyl acetate

3: 1.) CuBr*SMe₂, 2.) TMSCl / 1.) ether, -20 deg C, 15 min, 2.) ether, THF, -78 deg C, 1 h

With n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; dihydrogen peroxide; 1,1,1,3,3,3-hexamethyl-disilazane; In ethyl acetate;
DOI:10.1016/S0957-4166(00)82107-2

Reference yield:

: 919349-69-2
(S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 144564-16-9
tert-butyl (4S,5S)-4-allyl-5-((tert-butyldiphenylsilyl)oxymethyl)-2-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 30percent H₂O₂ / ethyl acetate

2: 1.) CuBr*SMe₂, 2.) TMSCl / 1.) ether, -20 deg C, 15 min, 2.) ether, THF, -78 deg C, 1 h

With chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; dihydrogen peroxide; In ethyl acetate;
DOI:10.1016/S0957-4166(00)82107-2