2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

Base Information

• Chemical Name: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate
• CAS No.: 443915-94-4
• Molecular Formula: C₂₉H₃₁N₃O₆
• Molecular Weight: 517.582
• Mol file: 443915-94-4.mol

Synonyms:2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

Chemical Property of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

There total 4 articles about 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate 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:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (443915-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃, cerium ammonium nitrate (CAN) / acetonitrile / 2.5 h

2: acetic acid / 8 h / 100 °C

With sodium azide; ammonium cerium(IV) nitrate; In acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(00)79826-1

Reference yield:

sodium acetate (127-09-3) + 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl nitrate (99049-59-9) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (443915-94-4)

Guidance literature:

In acetic acid; at 100 ℃; for 8h;

DOI:10.1016/S0040-4039(00)79826-1

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + [bis(acetoxy)iodo]benzene (3240-34-4) → C29H31N3O6 + 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (443915-94-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; at -30 ℃; Overall yield = 56 %;

DOI:10.1039/c7ra08637g

upstream raw materials:

sodium acetate

2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl nitrate

acetic anhydride

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside