4-Nitrophenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranoside
• CAS No.: 13089-23-1
• Molecular Formula: C₂₀H₂₄N₂O₁₁
• Molecular Weight: 468.417
• Mol file: 13089-23-1.mol

Synonyms:Glucopyranoside,p-nitrophenyl 2-acetamido-2-deoxy-, triacetate (ester), a-D- (7CI,8CI)

Chemical Property of 4-Nitrophenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranoside

Chemical Property:

• Melting Point: 191-193°C
• Boiling Point: 654.4±55.0 °C(Predicted)
• PKA: 13.22±0.70(Predicted)
• PSA: 172.28000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 1.54380

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: p-Nitrophenyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside (cas# 13089-23-1) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranoside

There total 31 articles about 4-Nitrophenyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-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: 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: 54.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (76375-60-5) → p-nitrophenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside (135266-95-4,13089-23-1)

Guidance literature:

With iron(III) chloride; calcium sulfate; In 1,2-dichloro-ethane; stereoselective reaction; Reflux; Inert atmosphere; Large scale reaction;

DOI:10.1016/j.carres.2008.09.003

Reference yield: 50.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9) → C20H24N2O11 (13089-23-1)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 20 ℃; for 4h;

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

Refernces

• 1、 Iino,Yoshida. "Chromatography of β-glucuronidase from bovine liver. A study of the enzyme binding sites of prepared adsorbents". . p. 1852 - 1859. Retrieved 1992.
• 2、 Zhang, Qing,Li, Zhonghua,Chernova, Tatiana,Saikam, Varma,Cummings, Richard,Song, Xuezheng,Ju, Tongzhong,Smith, David F.,Wang, Peng G.. "Synthesis and Characterization of Versatile O-Glycan Precursors for Cellular O-Glycomics". . p. 2507 - 2513. Retrieved 2019/11/13.
• 3、 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.