(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

Base Information

Chemical Name:(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester
CAS No.:220657-13-6
Molecular Formula:C₃₃H₄₈N₂O₉Si
Molecular Weight:644.838
Hs Code.:

(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

Synonyms:(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

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Chemical Property of (2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

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Technology Process of (2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

There total 4 articles about (2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl 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: 64.0%

: 2899-07-2
(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine

: 126587-71-1
Boc-threonine [(2-trimethylsilyl)ethoxy]methyl ester

: 220657-13-6
(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

Guidance literature:: With dmap; Isopropenyl chloroformate; triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(98)01042-4

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 220657-13-6
(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: KOH; Bu₄NHSO₄ / tetrahydrofuran / 0.5 h / 0 °C

1.2: H₂O / tetrahydrofuran / 5 h / 20 °C

2.1: 60 percent / Et₃N; DMAP; isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

With dmap; potassium hydroxide; Isopropenyl chloroformate; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0530023

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 220657-13-6
(2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / KOH; tetrabutylammonium hydrogen sulfate / tetrahydrofuran / 0.5 h / 0 °C

2: 60 percent / triethylamine; 4-(dimethylamino)pyridine; isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

With dmap; potassium hydroxide; Isopropenyl chloroformate; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo070412r