Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 7. Conversion of thiocarbonates into deoxy-sugars
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 15 (15) , 1718-1723
- https://doi.org/10.1039/p19770001718
Abstract
Radical-initiated reduction of five- or six-membered ring thiocarbonates, followed by alkaline hydrolysis, affords a convenient synthesis of 2-, 3-, 4-, and 5-deoxy-sugars. For 5,6- and 4,6-thiocarbonates the regiospecificity of the reaction complements the recently developed synthesis of 6-deoxy-sugars by ring opening of the same thiocarbonates with methyl iodide. Applications in the synthesis of 2-deoxy-D-ribose and 2′-deoxyadenosine are described.This publication has 1 reference indexed in Scilit:
- Synthesis of deoxysugars and of deoxynucleosides from diol thiocarbonatesJournal of the Chemical Society, Chemical Communications, 1976