(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 26295-42-1
• Molecular Formula: C₂₂H₂₅N₃O₉
• Molecular Weight: 475.455
• Mol file: 26295-42-1.mol

Synonyms:(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 24 articles about (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-phenyl-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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%

phenylacetylene (536-74-3) + 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → 1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose (26295-42-1,26295-46-5)

Guidance literature:

With [(PPh₃)₂Cu(μ-2,2'-thiodiacetato)Cu(PPh₃)₂]*6H₂O; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1039/c7dt02346d

Reference yield: 95.0%

phenylpropyolic acid (637-44-5) + 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → 1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose (26295-42-1,26295-46-5)

Guidance literature:

With copper(l) iodide; potassium carbonate; at 60 ℃; for 0.833333h;

Reference yield: 95.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) + phenylacetylene (536-74-3) → 1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose (26295-42-1,26295-46-5)

Guidance literature:

D-Glucose; acetic anhydride; With iodine; at 20 ℃;

With hydrogen bromide; In dichloromethane; acetic acid; at 20 ℃; for 1h;

phenylacetylene; With sodium azide; sodium hydrogencarbonate; sodium L-ascorbate; tetra(n-butyl)ammonium hydrogensulfate; copper(II) sulfate; In ethanol; chloroform; water; at 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2005.01.175

upstream raw materials:

phenylacetylene

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

D-Glucose

acetic anhydride

Downstream raw materials:

[1-(β-D-galactopyranosyl)-1H-1,2,3-triazol-4-yl]-benzene

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-phenyltriazol-1-yl)tetrahydropyran-3,4,5-triol

Refernces

• 1、 Jain, Yachana,Kumari, Mitlesh,Singh, Raman Preet,Kumar, Deepak,Gupta, Ragini. "Sonochemical Decoration of Graphene Oxide with Magnetic Fe3O4@CuO Nanocomposite for Efficient Click Synthesis of Coumarin-Sugar Based Bioconjugates and Their Cytotoxic Activity". . p. 1142 - 1154. Retrieved 2020.
• 2、 Rossi, Lauren L.,Basu, Amit. "Glycosidase inhibition by 1-glycosyl-4-phenyl triazoles". . p. 3596 - 3599. Retrieved 2005.
• 3、 Chittaboina, Srinivas,Xie, Fang,Wang, Qian. "One-pot synthesis of triazole-linked glycoconjugates". . p. 2331 - 2336. Retrieved 2005.
• 4、 Li, Yaru,Sun, Ziru,Cui, Yujun,Zhang, Heming,Zhang, Shunjie,Wang, Xinyu,Liu, Shengnan,Gao, Qingzhi. "Oxaliplatin derived monofunctional triazole-containing platinum(II) complex counteracts oxaliplatin-induced drug resistance in colorectal cancer". . . Retrieved 2021/01/25.