1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE
• CAS No.: 171032-74-9
• Molecular Formula: C14H19N3O9
• Molecular Weight: 373.32
• Mol file: 171032-74-9.mol

Synonyms:1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE;2-Azido-2-deoxy-D-glucopyranose 1,3,4,6-Tetraacetate

Chemical Property of 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE

Chemical Property:

• PSA: 164.18000
• LogP: -0.16744
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Azido-2-deoxy-D-glucopyranose 1,3,4,6-Tetraacetate is used in the investigation of cellular metabolism of synthetic azidosugars.

Technology Process of 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE

There total 18 articles about 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-D-GLUCOPYRANOSE 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: 100.0%

2-azido-2-deoxy-D-glucose + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9)

Guidance literature:

With pyridine; at 20 ℃; for 10h;

DOI:10.1021/jo202322k

Reference yield: 92.0%

(+)-D-glucosamine hydrochloride (1078691-95-8) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9)

Guidance literature:

(+)-D-glucosamine hydrochloride; With potassium carbonate; copper(II) sulfate; In methanol; at 20 ℃; for 2h;

acetic anhydride; With pyridine; for 3h; Further stages.;

DOI:10.1021/ol701581g

Reference yield: 85.0%

D-glucosamine hydrochloride (14131-63-6) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9)

Guidance literature:

D-glucosamine hydrochloride; With copper(ll) sulfate pentahydrate; triflic azide; triethylamine; In water; at 20 ℃; for 18h;

acetic anhydride; With pyridine; dmap; at 20 ℃; for 18h;

upstream raw materials:

acetic anhydride

acetic acid

D-glucal triacetate

3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Downstream raw materials:

phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside

p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thio-α-D-glucopyranoside

4-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside