(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1403577-47-8
Molecular Formula:C₃₃H₄₉NO₆Si
Molecular Weight:583.841
Hs Code.:

(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 10 articles about (2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-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: 70.0%

: 1403577-33-2
(2S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-2-methoxymethoxymethyl-4-methyl-3-oxopyrrolidine-1-carboxylic acid tert-butyl ester

: 1730-25-2
allylmagnesium bromide

: 1403577-17-2
(2S,3S,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1403577-47-8
(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In diethyl ether; at -78 ℃; for 2h;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j

Reference yield:

: (S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

: 1403577-17-2
(2S,3S,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1403577-47-8
(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: lithium bromide; toluene-4-sulfonic acid

2: borane-THF / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

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

4: diethyl ether / 2 h / -78 °C

With borane-THF; Dess-Martin periodane; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j

Reference yield:

: C₁₈H₂₉NO₆

: 1403577-17-2
(2S,3S,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1403577-47-8
(2S,3R,4S)-3-allyl-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: lithium borohydride / diethyl ether; methanol / 16 h / Inert atmosphere

2: lipoprotein lipase from Pseudomonas / 48 h / 37 °C / Enzymatic reaction

3: 1H-imidazole; dmap / dichloromethane / 2 h / Inert atmosphere

4: potassium carbonate; methanol

5: lithium bromide; toluene-4-sulfonic acid

6: borane-THF / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

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

8: diethyl ether / 2 h / -78 °C

With 1H-imidazole; methanol; dmap; lithium borohydride; borane-THF; lipoprotein lipase from Pseudomonas; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j