(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:637338-14-8
Molecular Formula:C₂₅H₃₃NO₃Si
Molecular Weight:423.627
Hs Code.:

Synonyms:(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 1 articles about (2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl 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%

: 1113-12-8
diallyl(dimethyl)silane

: 59830-60-3
benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

: 637338-14-8
(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: benzyl (1S)-(1-formyl-2-phenylethyl)carbamate; With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 0.333333h;

diallyl(dimethyl)silane; In dichloromethane; at -10 ℃; for 2h;
DOI:10.1055/s-2003-41433

Reference yield: 85.0%

: 108-24-7
acetic anhydride

: 637338-14-8
(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

: 637338-15-9
(2S,3S,5S)-3-Acetoxy-5-(allyl-dimethyl-silanylmethyl)-2-benzyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1055/s-2003-41433

Reference yield:

: 637338-14-8
(2S,3S,5S)-5-(Allyl-dimethyl-silanylmethyl)-2-benzyl-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

: (2S,3S,5S)-2-Benzyl-3-hydroxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

2.1: Br₂ / CH₂Cl₂

2.2: HF*pyridine / CH₂Cl₂ / 3 h / 20 °C

3.1: 286 mg / KHCO₃; KF; aq. H₂O₂ / tetrahydrofuran; methanol / 10 h / 20 °C

4.1: KOH

With dmap; potassium fluoride; potassium hydroxide; dihydrogen peroxide; bromine; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-2003-41433