2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-alpha-D-galactopyranosyl cyanide

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-alpha-D-galactopyranosyl cyanide
• CAS No.: 168567-90-6
• Molecular Formula: C₁₅H₁₈N₄O₉
• Molecular Weight: 398.329
• European Community (EC) Number: 687-315-2
• DSSTox Substance ID: DTXSID60471237
• Nikkaji Number: J898.516B
• Wikidata: Q76421925
• Mol file: 168567-90-6.mol

Synonyms:168567-90-6;2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-alpha-D-galactopyranosyl cyanide;[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-azido-6-cyanooxan-2-yl]methyl acetate;beta-D-galacto-2-Heptulopyranosononitrile, 2-azido-2-deoxy-, 3,4,5,7-tetraacetate;DTXSID60471237;AKOS025294693;2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy- alpha -D-galactopyranosyl cyanide;2,3,4,6-TETRA-O-ACETYL-1-AZIDO-1-DEOXY-A-D-GALACTOPYRANOSYL CYANIDE;2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-alpha-D-galactopyranosyl cyanide, >=98.0% (HPLC);(2R,3R,4S,5S,6R)-6-[(Acetyloxy)methyl]-2-azido-2-cyanooxane-3,4,5-triyl triacetate (non-preferred name)

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

Chemical Property:

• PSA: 187.97000
• LogP: -0.27366
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 398.10737816
• Heavy Atom Count: 28
• Complexity: 754

Purity/Quality:

98%Min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-a-D-galactopyranosyl cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 7235305
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 1 articles about 2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-alpha-D-galactopyranosyl cyanide 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: 96.0%

2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide (83497-42-1) → 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-α-D-galactopyranosylcyanide (168567-90-6)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 0.0833333h; Ambient temperature;

DOI:10.1016/0040-4020(96)00440-1

Reference yield: 80.0%

triphenylphosphine (603-35-0) + 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-α-D-galactopyranosylcyanide (168567-90-6) → (1R)2,3,4,6-tetra-O-acetyl-1-(3-triphenylphosphazido)-D-galactopyranosyl cyanide

Guidance literature:

In diethyl ether; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4020(97)01055-7

Reference yield: 72.0%

2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-α-D-galactopyranosylcyanide (168567-90-6) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-azido-2-carbamoyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With dichlorotetrakis(dimethylsulfoxide)ruthenium; In 1-methyl-pyrrolidin-2-one; water; at 105 ℃; for 8h; chemoselective reaction;

DOI:10.1016/j.tetlet.2015.09.040

upstream raw materials:

2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-galactopyranosyl cyanide

Downstream raw materials:

(-)-(5R,6R)-3,5-Bis(acetoxy)-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one

Refernces

• 1、 Somsak, Laszlo,Sos, Erzsebet,Gyoergydeak, Zoltan,Praly, Jean-Pierre,Descotes, Gerard. "Synthesis and some transformations of 1-azido-glycopyranosyl cyanides - Precursors of anomeric α-amino acids". . p. 9121 - 9136. Retrieved 1996.