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

Base Information

• Chemical Name: O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide
• CAS No.: 845810-56-2
• Molecular Formula: C₃₁H₃₅N₃O₁₅
• Molecular Weight: 689.63
• Mol file: 845810-56-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide 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: 40.0%

Nα-benzyloxycarbonyl-L-seryl-p-nitroanilide (108653-47-0) + O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) → O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide (845810-56-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 16h;

DOI:10.1039/b412030b

Reference yield:

benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamate (845810-54-0) → O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide (845810-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 20 °C

2: 40 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b412030b

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyl-N-benzyloxycarbonyl-L-serine-p-nitroanilide (845810-56-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 20 °C

4: 40 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b412030b

upstream raw materials:

Nα-benzyloxycarbonyl-L-seryl-p-nitroanilide

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

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

N-(benzyloxycarbonyl)-L-serine