(2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester

Base Information

• Chemical Name: (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester
• CAS No.: 191655-44-4
• Molecular Formula: C₂₂H₃₇NO₅Si
• Molecular Weight: 423.625
• Mol file: 191655-44-4.mol

Synonyms:(2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester

Chemical Property of (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester

There total 2 articles about (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric 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: 93.0%

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate (105183-60-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester (191655-44-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1039/c9sc01405e

Reference yield:

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester (30925-18-9) → (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester (191655-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.17 h / -15 °C

1.2: 99.4 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -15 °C

2.1: 76 percent / Et₃N; 4-DMAP / CH₂Cl₂

With 4-methyl-morpholine; dmap; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.08.029

Reference yield: 75.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) + (2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester (191655-44-4) → C23H32N2O7SSi

Guidance literature:

(2S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethyl-silanyloxy)-butyric acid benzyl ester; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 4.5h;

4-Nitrobenzenesulfonyl chloride; With sodium hydrogencarbonate; In water; ethyl acetate; for 8h;

upstream raw materials:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

tert-butyldimethylsilyl chloride

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

Downstream raw materials:

(2S)-N'-(2-tert-butoxycarbonylamino-4-hydroxy-butyryl)-N-methyl-hydrazinecarboxylic acid benzyl ester

(2S)-N'-[2-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyryl]-N-methyl-hydrazinecarboxylic acid benzyl ester

tert-butyl 7-(N³-benzoylthymin-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate

tert-butyl 7-(N³-benzoyluracil-1-yl)-5S-[N-(tert-butoxycarbonyl)amino]-3-oxaheptanate