1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose
• CAS No.: 84278-00-2
• Molecular Formula: C14H19 N3 O9
• Molecular Weight: 373.32
• European Community (EC) Number: 633-035-0
• DSSTox Substance ID: DTXSID10447866
• Nikkaji Number: J774.536B
• Mol file: 84278-00-2.mol

Synonyms:84278-00-2;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose;[(2R,3R,4R,5R)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate;2-AZIDO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-ALPHA/BETA-D-GALACTOPYRANOSE;2-Azido-D-galactose tetraacetate;2-Azido-2-deoxy-D-galactose tetraacetate;SCHEMBL18857676;DTXSID10447866;QKGHBQJLEHAMKJ-RQICVUQASA-N;MFCD02683262;AKOS025295799;2-Azido-2-deoxy-D-galactopyranose tetraacetate;2-Azido-D-galactose tetraacetate, >=97% (HPLC);W-203910;2-azido-2-deoxy-1,3,4,6-tetra-O-acetyl-alpha,beta-D-galactopyranose

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

Chemical Property:

• Melting Point: 113-114°C
• PSA: 164.18000
• LogP: -0.16744
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 373.11212919
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

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

2-Azido-2-deoxy-1,3,4,6-tetra-O-acetyl-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-68
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H](C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

There total 13 articles about 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 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: 95.0%

acetic anhydride (108-24-7) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.1016/j.carres.2008.11.018

Reference yield: 95.0%

sodium acetate (127-09-3) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2)

Guidance literature:

In acetic acid; at 120 ℃; Inert atmosphere; Microwave irradiation;

DOI:10.1021/jacs.9b06830

Reference yield: 92.0%

acetic anhydride (108-24-7) + D-(+)-galactosamine hydrochloride (1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (84278-00-2)

Guidance literature:

D-(+)-galactosamine hydrochloride; With pyridine; sodium azide; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; triethylamine; In water; at 0 ℃; for 48h;

acetic anhydride; With pyridine; dmap; for 2h;

DOI:10.1002/cjoc.202100914

upstream raw materials:

mercury(II) diacetate

acetic anhydride

2-deoxy-2-azidogalactopyranose

triacetyl-D-galactal

Downstream raw materials:

3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside

phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside

phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α-D-galactopyranoside

Refernces

• 1、 Zhao, Jie,Liu, Jiazhi,Liu, Xinnan,Cao, Qi,Zhao, Hongbo,Liu, Lizhen,Ye, Farong,Wang, Can,Shao, Hong,Xue, Dongxiang,Tao, Houchao,Li, Bin,Yu, Biao,Wang, Ping. "Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation". supporting information. p. 787 - 793. Retrieved 2022/01/31.
• 2、 -. "Chondroitin sulfate oligosaccharides and preparation method and applications thereof". Paragraph 0094; 0114-0116. . Retrieved 2019/08/06.