2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside

Base Information

• Chemical Name: 2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside
• CAS No.: 140428-81-5
• Molecular Formula: C16H23N3O10
• Molecular Weight: 417.373
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20693716
• Mol file: 140428-81-5.mol

Synonyms:DTXSID20693716;2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside

Chemical Property of 2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside

Chemical Property:

• Melting Point: 113.0 to 117.0 °C
• PSA: 173.41000
• LogP: -0.15084
• Storage Temp.: 0-10°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 13
• Exact Mass: 417.13834394
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

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

2-Azidoethyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OCCN=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OCC1[C@H]([C@@H]([C@H]([C@@H](O1)OCCN=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside

There total 21 articles about 2-Azidoethyl (5xi)-2,3,4,6-tetra-O-acetyl-beta-D-xylo-hexopyranoside 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-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-78-9,85193-55-1,86651-32-3,86651-40-3) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With Caswell No_. 744A; In water monomer; for 16h; Reflux;

DOI:10.1039/c9dt02614b

Reference yield: 99.0%

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-77-8) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 85 ℃; for 5h;

Reference yield: 94.0%

2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (350793-49-6) → 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1002/1521-3765(20010504)7:9<1868::AID-CHEM1868>3.0.CO;2-H

upstream raw materials:

2-azidoethanol

β-D-glucose pentaacetate

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

C₄₆H₅₈N₈O₂₂

C₄₆H₅₈N₈O₂₂

C₃₀H₃₅N₅O₁₂

Refernces

• 1、 Nguyen, Kim-Anh,Peuchmaur, Marine,Magnard, Sandrine,Haudecoeur, Romain,Boyère, Cédric,Mounien, Saravanan,Benammar, Ikram,Zampieri, Veronica,Igonet, Sébastien,Chaptal, Vincent,Jawhari, Anass,Boumendjel, Ahcène,Falson, Pierre. "Glycosyl-Substituted Dicarboxylates as Detergents for the Extraction, Overstabilization, and Crystallization of Membrane Proteins". . p. 2948 - 2952. Retrieved 2018.
• 2、 Eissa, Ahmed M.,Smith, Michael J.P.,Kubilis, Artur,Mosely, Jackie A.,Cameron, Neil R.. "Polymersome-forming amphiphilic glycosylated polymers: Synthesis and characterization". . p. 5184 - 5193. Retrieved 2013.
• 3、 Machida, Takuya,Novoa, Alexandre,Gillon, émilie,Zheng, Shuangshuang,Claudinon, Julie,Eierhoff, Thorsten,Imberty, Anne,R?mer, Winfried,Winssinger, Nicolas. "Dynamic Cooperative Glycan Assembly Blocks the Binding of Bacterial Lectins to Epithelial Cells". . p. 6762 - 6766. Retrieved 2017.
• 4、 Wo?niak, Marta,Pastuch-Gawo?ek, Gabriela,Makuch, Sebastian,Wi?niewski, Jerzy,Zió?kowski, Piotr,Szeja, Wies?aw,Krawczyk, Monika,Agrawal, Siddarth. "Overcoming hypoxia-induced chemoresistance in cancer using a novel glycoconjugate of methotrexate". . p. 1 - 16. Retrieved 2021.
• 5、 Belmonte-Reche, Efres,Benassi, Alessandra,Cucchiarini, Anne,Doria, Filippo,Freccero, Mauro,Gabelica, Valerie,Mergny, Jean Louis,Morales, Juan Carlos,Guédin, Aurore,Pe?alver, Pablo,Rosu, Frèdèric. "Thiosugar naphthalene diimide conjugates: G-quadruplex ligands with antiparasitic and anticancer activity". . . Retrieved 2022/02/17.
• 6、 Baek, Seung-Yeol,Baik, Mu-Hyun,Choe, Wonyoung,Hong, Sung You,Jeon, Ji Hwan,Jeong, Seo Yeong,Kim, Woo Gyum,Nam, Dongsik. "Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition". supporting information. p. 3374 - 3381. Retrieved 2020/05/14.