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

Base Information

Chemical Name:(2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxy-methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate
CAS No.:1334590-01-0
Molecular Formula:C₂₁H₃₃NO₆Si
Molecular Weight:423.582
Hs Code.:

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

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

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

There total 6 articles about (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxy-methyl)-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: 73.0%

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

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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; regioselective reaction;
DOI:10.1021/jo201453x

Reference yield:

: 1334589-99-9
(2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyl-dimethylsilyloxy)methyl)-5-oxopyrrolidine-2-carboxylate

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

1.2: 20 °C

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

With sodium hydride; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo201453x

Reference yield:

: 159970-68-0
(2R,5S)-2-(tert-butyl)-1-ethoxycarbonylacetyl-5-methoxycarbonyl-1,3-oxazolidine

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

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium tert-butylate / tert-butyl alcohol / Reflux

2.1: sodium tetrahydroborate / tetrahydrofuran; acetic acid / 20 °C

3.1: hydrogenchloride; 2,2,2-trifluoroethanol / 1.3-propanedithiol

4.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

5.2: 20 °C

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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; 2,2,2-trifluoroethanol; potassium tert-butylate; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; 1.3-propanedithiol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 1.1: Dieckmann condensation;
DOI:10.1021/jo201453x