(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:855517-79-2
Molecular Formula:C₃₂H₄₅NO₇Si
Molecular Weight:583.797
Hs Code.:

(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 5 articles about (3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 73.0%

: 855517-78-1
(3S,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 855517-79-2
(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (3S,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.666667h;

With acetic acid; In tetrahydrofuran; cooling;
DOI:10.1016/j.tet.2005.03.042

Reference yield:

: 855517-77-0
(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 5437-45-6
Benzyl bromoacetate

: 855517-78-1
(3S,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 855517-79-2
(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

Benzyl bromoacetate; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.tet.2005.03.042

Reference yield:

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 855517-79-2
(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: CuBr*Me₂S / tetrahydrofuran / 0.5 h / cooling

1.2: 90 percent / trimethylsilyl chloride / tetrahydrofuran / -78 - 20 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1.50 g / tetrahydrofuran / -78 - 20 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.67 h / -78 °C

3.2: 73 percent / acetic acid / tetrahydrofuran / cooling

With copper(I) bromide dimethylsulfide complex; lithium hexamethyldisilazane; In tetrahydrofuran; 1.2: Michael addition;
DOI:10.1016/j.tet.2005.03.042