4-Nitrophenyl2-acetamido-2-deoxy-4,6-O-benzylidene-b-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl2-acetamido-2-deoxy-4,6-O-benzylidene-b-D-glucopyranoside
• CAS No.: 19234-58-3
• Molecular Formula: C21H22 N2 O8
• Molecular Weight: 430.41
• Mol file: 19234-58-3.mol

Synonyms:Glucopyranoside,p-nitrophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-, b-D- (8CI);Pyrano[3,2-d]-1,3-dioxin, b-D-glucopyranoside deriv.

Chemical Property of 4-Nitrophenyl2-acetamido-2-deoxy-4,6-O-benzylidene-b-D-glucopyranoside

Chemical Property:

• Melting Point: 258-261?C (dec.)
• PSA: 132.07000
• LogP: 2.59240
• Solubility.: DMF, DMSO

Purity/Quality:

99%, ^*data from raw suppliers

4-Nitrophenyl 2-acetamido-2-deoxy-4,6-O-benzylidene-b-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-4,6-benzylidene-β-D-glucopyranoside (cas# 19234-58-3) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl2-acetamido-2-deoxy-4,6-O-benzylidene-b-D-glucopyranoside

There total 4 articles about 4-Nitrophenyl2-acetamido-2-deoxy-4,6-O-benzylidene-b-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: 96.0%

benzaldehyde dimethyl acetal (1125-88-8) + 4-nitrophenyl N-acetyl-β-D-glucosaminide (3459-18-5,50645-66-4) → 4-nitrophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (19234-58-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1016/j.carres.2007.05.023

Reference yield:

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (13089-27-5,13089-23-1) → 4-nitrophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (19234-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaOCH₃; MeOH / CHCl₃

2: 96 percent / 4-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

With methanol; sodium methylate; toluene-4-sulfonic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2007.05.023

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 4-nitrophenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (19234-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 20 °C

1.2: 44 percent / K₂CO₃ / acetone / 55 °C

2.1: 97 percent / NaOCH₃; MeOH / CHCl₃

3.1: 96 percent / 4-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

With methanol; sodium methylate; toluene-4-sulfonic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2007.05.023

upstream raw materials:

benzaldehyde dimethyl acetal

4-nitrophenyl N-acetyl-β-D-glucosaminide

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

4-nitro-phenol

Downstream raw materials:

4-nitrophenyl 2-acetamido-5-S-acetyl-4,6-di-O-acetyl-2-deoxy-3-thio-β-D-glucopyranoside

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