(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

Base Information

Chemical Name:(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate
CAS No.:1334590-03-2
Molecular Formula:C₂₄H₃₇NO₆Si
Molecular Weight:463.646
Hs Code.:

Synonyms:(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

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Chemical Property of (3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

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Technology Process of (3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

There total 8 articles about (3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-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: 87.0%

: 1334590-02-1
(2S,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-formyl-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

: 13291-18-4
isopropenylmagnesium bromide

: 1334590-03-2
(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

Guidance literature:: With chloro-trimethyl-silane; In tetrahydrofuran; at -40 ℃; for 2h; stereoselective reaction;
DOI:10.1021/jo201453x

Reference yield:

: 1334590-00-9
(2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

: 1334590-03-2
(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane; water / 20 °C

2: Dess-Martin periodane / dichloromethane / 0 - 20 °C

3: chloro-trimethyl-silane / tetrahydrofuran / 2 h / -40 °C

With chloro-trimethyl-silane; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo201453x

Reference yield:

: 1334590-01-0
(2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxy-methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

: 1334590-03-2
(3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((S)-1-hydroxy-2-methylallyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

2: chloro-trimethyl-silane / tetrahydrofuran / 2 h / -40 °C

With chloro-trimethyl-silane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo201453x