2-Acetamido-1-bromoacetamido-1,2-dideoxy-B-D-glucopyranoside

Base Information

• Chemical Name: 2-Acetamido-1-bromoacetamido-1,2-dideoxy-B-D-glucopyranoside
• CAS No.: 73982-43-1
• Molecular Formula: C10H17 Br N2 O6
• Molecular Weight: 341.159
• Mol file: 73982-43-1.mol

Synonyms:2-Acetamido-1-bromoacetamido-1,2-dideoxy-B-D-glucopyranoside

Chemical Property of 2-Acetamido-1-bromoacetamido-1,2-dideoxy-B-D-glucopyranoside

Chemical Property:

• PSA: 128.12000
• LogP: -1.77700

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Acetamido-1-bromoacetamido-1,2-dideoxy-B-D-glucopyranoside

There total 2 articles about 2-Acetamido-1-bromoacetamido-1,2-dideoxy-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: 73.0%

bromoacetic anhydride (13094-51-4) + 2-acetamido-2-deoxy-β-D-glucopyranosylamine (4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1) → 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine (73982-43-1)

Guidance literature:

In methanol; benzene; 1.) 1.5 h, 0 deg C, 2.) 1.5 h, RT;

DOI:10.1016/S0008-6215(00)85318-5

Reference yield:

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) → 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine (73982-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium hydrogen carbonate

2: dimethylsulfoxide

With ammonium bicarbonate; In dimethyl sulfoxide;

DOI:10.1002/1097-458X(200102)39:2<98::AID-MRC792>3.0.CO;2-3

Reference yield: 73.0%

C71H88N14O16S + 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine (73982-43-1) → C81H104N16O22S

Guidance literature:

With 1,4-dithiothreitol; In aq. phosphate buffer; at 20 ℃; for 0.833333h; pH=7.4;

DOI:10.1248/cpb.c18-00626

upstream raw materials:

bromoacetic anhydride

2-acetamido-2-deoxy-β-D-glucopyranosylamine

N-Acetyl-D-glucosamine

Downstream raw materials:

N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide

Refernces

• 1、 Malik, Jayshri J.,Risley, John M.. "Synthesis of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues". . p. 98 - 100. Retrieved 2007/10/03.
• 2、 Paul,Bernacki,Korytnyk. "Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-beta-D-glycopyranosylamine derivatives and related analogs.". . p. 99 - 115. Retrieved 2007/10/02.