2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide
• CAS No.: 53784-33-1
• Molecular Formula: C11H15 N3 O7
• Molecular Weight: 301.256
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID10369332
• Nikkaji Number: J1.363.048H
• Wikidata: Q82156377
• Mol file: 53784-33-1.mol

Synonyms:53784-33-1;2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide;[(3R,4S,5R,6R)-4,5-diacetyloxy-6-azidooxan-3-yl] acetate;2,3,4-TRI-O-ACETYL-b-D-XYLOPYRANOSYL AZIDE;ST50306943;DTXSID10369332;LMAJKBXVWKPVDF-LMLFDSFASA-N;.beta.-D-Xylopyranosyl azide, 2,3,4-triacetate;2,3,4-Tri-O-acetyl- beta -D-xylopyranosyl azide;2-O,3-O,4-O-Triacetyl-beta-D-xylopyranosyl azide;2,3,4-tri-O-acetyl-1-azido-1-deoxy-beta-D-xylopyranose;(2R,3R,4S,5R)-2-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate;2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide, >=98.0% (HPLC)

Chemical Property of 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide

Chemical Property:

• Melting Point: 84°C
• Refractive Index: 1.4930 (estimate)
• Boiling Point: 442.39°C (rough estimate)
• PSA: 137.88000
• Density: 1.3759 (rough estimate)
• LogP: -0.09914
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 301.09099983
• Heavy Atom Count: 21
• Complexity: 474

Purity/Quality:

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

2,3,4-Tri-O-acetyl-b-D-xylopyranosyl azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)N=[N+]=[N-]
• Isomeric SMILES: CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)N=[N+]=[N-]

Technology Process of 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide

There total 12 articles about 2,3,4-Tri-O-acetyl-beta-D-xylopyranosyl azide 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: 99.0%

tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose (53784-33-1)

Guidance literature:

tetra-O-acetyl-β-D-xylopyranose; With trimethylsilylazide; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With tin(IV) chloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/c8ob02810a

Reference yield: 90.0%

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose (53784-33-1)

Guidance literature:

D-Xylose; acetic anhydride; With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With sodium azide; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200500646

Reference yield: 88.0%

1,2,3,4-tetra-O-acetyl-D-xylopyranose (62446-93-9) → 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose (53784-33-1)

Guidance literature:

With trimethylsilylazide; tin(IV) chloride; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.10.004

upstream raw materials:

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

diethyl ether

D-Xylose

acetic anhydride

Downstream raw materials:

4-phenyl-1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1H-[1,2,3]triazole

C₅₃H₆₇N₇O₁₂

C₅₃H₆₇N₇O₁₂

1-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4-(4-nitrophenyl)-1,2,3-triazole

Refernces

• 1、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 2、 Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao. "Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II". . p. 383 - 390. Retrieved 2019/12/30.