1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Base Information

• Chemical Name: 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose
• CAS No.: 185114-94-7
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Mol file: 185114-94-7.mol

Synonyms:1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Chemical Property of 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

There total 3 articles about 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose 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%

acetic anhydride (108-24-7) + 3-azido-3-deoxy-D-glucopyranose (104875-44-7) → 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 3h; Cooling with ice;

DOI:10.1016/j.tet.2012.10.058

Reference yield: 94.0%

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (27581-57-3) + acetic anhydride (108-24-7) → 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0)

Guidance literature:

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h;

acetic anhydride; With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2005.05.058

Reference yield: 85.0%

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose (13964-23-3) + acetic anhydride (108-24-7) → 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0)

Guidance literature:

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose; In methanol; water; Reflux;

acetic anhydride; With pyridine; at 20 ℃; for 1h;

DOI:10.1080/15257770.2012.696759

upstream raw materials:

acetic anhydride

3-azido-3-deoxy-D-glucopyranose

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose

Refernces

• 1、 Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong. "Glucose positions affect the phloem mobility of glucose-fipronil conjugates". . p. 6065 - 6071. Retrieved 2015/04/22.
• 2、 Manta, Stella,Parmenopoulou, Vanessa,Kiritsis, Christos,Dimopoulou, Athina,Kollatos, Nikolaos,Papasotiriou, Ioannis,Balzarini, Jan,Komiotis, Dimitri. "Stereocontrolled facile synthesis and biological evaluation of (3 S) and (3 R)-3-Amino (and Azido)-3-deoxy pyranonucleosides". experimental part. p. 522 - 535. Retrieved 2012/10/08.