2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate

Base Information

• Chemical Name: 2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate
• CAS No.: 136172-58-2
• Molecular Formula: C24H27N3O7
• Molecular Weight: 469.494
• European Community (EC) Number: 856-101-2
• Mol file: 136172-58-2.mol

Synonyms:136172-58-2;2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate;[6-acetyloxy-5-azido-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate;D-Glucopyranose, 2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-, 1,6-diacetate

Chemical Property of 2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate

Chemical Property:

• PSA: 130.04000
• LogP: 3.13996
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 469.18490021
• Heavy Atom Count: 34
• Complexity: 703

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OCC2=CC=CC=C2)OCC3=CC=CC=C3

Technology Process of 2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate

There total 21 articles about 2-Azido-2-deoxy-3,4-bis-O-(phenylmethyl)-D-glucopyranose 1,6-diacetate 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%

acetic anhydride (108-24-7) + 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose (136172-58-2)

Guidance literature:

trifluoroacetic acid; In toluene; at 18 - 50 ℃;

Reference yield:

acetic anhydride (108-24-7) + methyl-2-azido-3,4,5-tri-O-benzyl-2-desoxy-α-D-glucopyranoside (95015-29-5) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose (136172-58-2)

Guidance literature:

With sulfuric acid; In acetic acid; at 15 ℃; Heating; Large scale;

Reference yield:

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (67546-20-7) → 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose (136172-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaH / dimethylformamide

2: TFA / 0 - 20 °C

With sodium hydride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja045613g

upstream raw materials:

acetic anhydride

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

benzyl bromide

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Downstream raw materials:

6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose

6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose

ethyl 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide