(4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: (4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 13089-27-5
• Molecular Formula: C20H24 N2 O11
• Molecular Weight: 468.417
• Hs Code.: 29389090
• Mol file: 13089-27-5.mol

Synonyms:Glucopyranoside,p-nitrophenyl 2-acetamido-2-deoxy-, 3,4,6-triacetate, b-D- (6CI,8CI); p-Nitrophenyl2-acetamido-2-deoxy-b-D-glucopyranoside triacetate

Chemical Property of (4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Melting Point: 238℃
• PSA: 172.28000
• LogP: 1.54380

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is useful substrate for the rapid colorimetric assay of N-Acetyl-beta-glucosaminidase in human urine Useful substrate for the rapid colorimetric assay of N-Acetyl-beta-glucosaminidase in human urine.

Technology Process of (4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

There total 12 articles about (4'-NITRO)PHENYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE 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: 89.0%

→ p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; water; for 1h;

Reference yield: 86.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1)

Guidance literature:

With dibenzo-18-crown-6; potassium carbonate; In acetonitrile; at 25 ℃; for 5h;

DOI:10.1023/B:RUBI.0000030138.26142.4b

Reference yield: 44.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + acetyl chloride (75-36-5) → p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1)

Guidance literature:

N-Acetyl-D-glucosamine; acetyl chloride; at 20 ℃;

4-nitro-phenol; With potassium carbonate; In acetone; at 55 ℃; Further stages.;

DOI:10.1016/j.carres.2007.05.023

upstream raw materials:

4-nitro-phenol

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

acetic anhydride

Downstream raw materials:

4-nitrophenyl β-D-fucopyranosyl-(1→4)-β-D-2-acetamido-2-deoxy-glucopyranoside

4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-2-acetamido-2-deoxy-glucopyranoside

5-(-N-(p-O-(N'-acetyl-(β-D-glucosaminyl)phenyl)aminocarbonyl))-2,2'-bipyridine

Refernces

• 1、 Wei, Jinhua,Lv, Xun,Lue, Yang,Yang, Gangzhu,Fu, Lifeng,Yang, Liu,Wang, Jianjun,Gao, Jianhui,Cheng, Shuihong,Duan, Qian,Jin, Cheng,Li, Xuebing. "Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library". supporting information. p. 2414 - 2419. Retrieved 2013/05/23.
• 2、 Chen, Hong-Ming,Withers, Stephen G.. "Syntheses of the 3- and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-β-d-gluco- and galactopyranoside". . p. 2212 - 2222. Retrieved 2008/02/12.