177186-23-1

Basic information

• Product Name: (1R,2R,4R,5R)-2,5-diazidocyclohexane-1,4-diol
• Synonyms: (1R,2R,4R,5R)-2,5-diazidocyclohexane-1,4-diol
• CAS NO: 177186-23-1
• Molecular Weight: 198.184
• Mol File: 177186-23-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2R,4R,5R)-2,5-diazidocyclohexane-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4R,5R)-2,5-diazidocyclohexane-1,4-diol(177186-23-1)
• EPA Substance Registry System: (1R,2R,4R,5R)-2,5-diazidocyclohexane-1,4-diol(177186-23-1)

Safety Data

• Hazardous Substances Data: 177186-23-1(Hazardous Substances Data)

Upstream product

• 285-52-9 cis-4,8-dioxa-tricyclo[5.1.0.0^3,5]octane 

Relevant articles and documents

Click Chemistry: Diverse Chemical Function from a Few Good Reactions

Examination of nature's favorite molecules reveals a striking preference for making carbon-heteroatom bonds over carbon-carbon bonds - surely no surprise given that carbon dioxide is nature's starting material and that most reactions are performed in water. Nucleic acids, proteins, and polysaccharides are condensation polymers of small subunits stitched together by carbon-heteroatom bonds. Even the 35 or so building blocks from which these crucial molecules are made each contain, at most, six contiguous C-C bonds, except for the three aromatic amino acids. Taking our cue from nature's approach, we address here the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach we call "click chemistry". Click chemistry is at once defined, enabled, and constrained by a handful of nearly perfect "spring-loaded" reactions. The stringent criteria for a process to earn click chemistry status are described along with examples of the molecular frameworks that are easily made using this spartan, but powerful, synthetic strategy.

Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives

A library of forty modified aminoglycosides was prepared in which the configuration and regiochemistry of two or three rings was widely varied. The library was based around three core ring systems: the 2-deoxystreptamine ring system found in the natural products, and both enantiomers of (1R*,2R*,4R*,5R*)-2,5-diamino-cyclohexane-1,4-diol and (1R*,3R*,4R*,6R*)-4,6-diaminocyclohexane-1,3-diol. In each case, the core was modified by glycosylation with one or two sugar rings. The absolute configuration of the sugar substituents (D or L), the configuration of the anomeric centres (α or β), and the regiochemical arrangement of the amine(s) were varied. The Royal Society of Chemistry 2005.