benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate

Base Information

• Chemical Name: benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate
• CAS No.: 845810-54-0
• Molecular Formula: C₂₃H₃₁N₃O₆Si
• Molecular Weight: 473.601
• Mol file: 845810-54-0.mol

Synonyms:benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate

Chemical Property of benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate

There total 4 articles about benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate 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: 80.0%

(S)-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid (104499-27-6,146346-84-1) + 4-nitro-aniline (100-01-6,104810-17-5) → benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate (845810-54-0)

Guidance literature:

With pyridine; trichlorophosphate; at -15 ℃; for 2h;

DOI:10.1039/b412030b

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate (845810-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / imidazole / dimethylformamide / 72 h / 60 °C

2: 80 percent / pyridine; POCl₃ / 2 h / -15 °C

With pyridine; 1H-imidazole; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1039/b412030b

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate (845810-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / aq. NaHCO₃ / tetrahydrofuran / 18 h

2: 77 percent / imidazole / dimethylformamide / 72 h / 60 °C

3: 80 percent / pyridine; POCl₃ / 2 h / -15 °C

With pyridine; 1H-imidazole; sodium hydrogencarbonate; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b412030b

upstream raw materials:

(S)-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

4-nitro-aniline

N-(benzyloxycarbonyl)-L-serine

benzyl chloroformate

Downstream raw materials:

Nα-benzyloxycarbonyl-L-seryl-p-nitroanilide

O-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide

O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide