4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside

Base Information

• Chemical Name: 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside
• CAS No.: 535960-64-6
• Molecular Formula: C₁₇H₁₉NO₁₀
• Molecular Weight: 397.339
• Mol file: 535960-64-6.mol

Synonyms:4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside

Chemical Property of 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside

There total 7 articles about 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside 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: 61.0%

vinyl acetate (108-05-4,9003-20-7) + p-nitrophenyl α-L-arabinofuranoside (22796-65-2,59495-69-1,99676-56-9,6892-58-6) → p-nitrophenyl 5-O-acetyl-α-L-arabinofuranoside + p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside (880491-85-0) + p-nitrophenyl 3,5-di-O-acetyl-α-L-arabinofuranoside (535960-65-7) + 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside (535960-64-6)

Guidance literature:

With Pseudomonas cepacia lipase LPS-30; In di-isopropyl ether; at 37 ℃; for 30h;

DOI:10.1016/j.bmc.2005.10.023

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1,2,3,5-tetra-O-acetyl-L-arabinofuranose (56272-01-6) → 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-β-L-arabino-hexofuranoside + 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside (535960-64-6)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2010.05.038

Reference yield:

p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside (880491-85-0) → 4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-α-L-arabino-hexofuranoside (535960-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Candida cylindracea lipase; aq. phosphate buffer / dimethylformamide / 7 h / 37 °C / pH 6

2: pyridine

With pyridine; Candida cylindracea lipase; phosphate buffer; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.10.023

upstream raw materials:

vinyl acetate

p-nitrophenyl α-L-arabinofuranoside

acetic anhydride

p-nitrophenyl 2,5-di-O-acetyl-α-L-arabinofuranoside

Downstream raw materials:

p-nitrophenyl 5-O-(4'-O-acetylferuloyl)-2,3-di-O-acetyl-α-L-arabinofuranoside

p-nitrophenyl 2,3-di-O-acetyl-α-L-arabinofuranoside

Refernces

• 1、 Mastihubova, Maria,Szemesova, Jana,Biely, Peter. "The acetates of p-nitrophenyl α-L-arabinofuranoside - Regioselective preparation by action of lipases". . p. 1805 - 1810. Retrieved 2007/10/03.