168567-91-7

Basic information

• Product Name: 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE
• Synonyms: 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE;2,3,4-Tri-O-acetyl-1-azido-1-deoxy-b-D-arabinopyranosylcyanide;2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-SS-D-ARABINOPYRANOSYL CYANIDE
• CAS NO: 168567-91-7
• Molecular Formula: C12H15N4O6
• Molecular Weight: 311.2707
• Mol File: 168567-91-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE(168567-91-7)
• EPA Substance Registry System: 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE(168567-91-7)

Safety Data

• Hazardous Substances Data: 168567-91-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE is used as a synthetic intermediate for the creation of various chemical compounds. Its unique structure, which includes a cyanide group and a sugar derivative, allows for the development of new molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE is used as a building block for the synthesis of new drug candidates. Its properties may contribute to the development of novel therapeutic agents, particularly in the area of antiviral or anticancer treatments, where its unique chemical structure could offer new avenues for drug design.
Used in Material Science:
2,3,4-TRI-O-ACETYL-1-AZIDO-1-DEOXY-BETA-D-ARABINOPYRANOSYL CYANIDE is also used in material science as a component in the synthesis of advanced materials. Its incorporation into these materials could lead to new properties, such as improved stability or enhanced reactivity, which could be beneficial in various applications, including catalysis or energy storage.

Upstream product

• 89158-09-8 2,3,4-tri-O-acetyl-1-deoxy-1-bromo-α-D-arabinopyranosyl cyanide 
• 83497-43-2 2,3,4-tri-O-acetyl-1-deoxy-1-bromo-β-D-xylopyranosyl cyanide 

Relevant articles and documents

Synthesis and some transformations of 1-azido-glycopyranosyl cyanides - Precursors of anomeric α-amino acids

Acetylated 1-azido-glycopyranosyl cyanides (of the (1R)- 2, and (1S)-D-galacto 16, (1S)-D-arabino 5, (1R)-D-gluco 7 (1R)-11, and (1S)-D-xylo 12 configurations) and C-(1-azido-1-deoxy-D-galactopyranosyl)formamide (19) were prepared from acetylated 1-halogeno-D-glycopyranosyl cyanides and formamide, resp., by sodium azide in dimethyl sulfoxide. Acetylated (1S)- 14 and (1R)- 15 1-chloro-D-galactopyranosyl cyanides were obtained from (1R)1-bromo-D-galactopyranosyl cyanide by lithium chloride in dimethyl sulfoxide. 1,3-Dipolar cycloaddition of axide ions to the cyano groups of 2 and 16 afforded acetylated 5-(1-azido-1-deoxy-α- and -β-D-galactopyranosyl)tetrazoles 3 and 17, resp., while that of dimethyl acetylene dicarboxylate to the azido moiety of 2 gave acetylated dimethyl 1-(1-azido-1-deoxy-β-D-galactopyranosyl)-1,2,3-triazole-4,5-dicarboxy late 20. Transformation of 3 by ethoxalyl chloride gave acetylated ethyl 2-(1-azido-1-deoxy-α-D-galactopyranosyl)-1,3,4-oxadiazole-5-carboxyla te 21.

Preparation and Photolysis of 1-Cyano-glycopyranosyl Azides

Treatment of 1-bromo-glycopyranosyl cyanides 1 and 4 with sodium azide in dimethyl sulfoxide gave 1-cyano-glycopyranosyl azides 2 and 5 in high yield, which on photolysis resulted in new oxazepine derivatives 3 and 6.