Efficient synthesis of 2-deoxy L-ribose from L-arabinose: mechanistic information on the 1,2-acyloxy shift in alkyl radicals.
[formula: see text] Conversion of the inexpensive L-arabinose 1 into the ethylthio ortho ester 7 followed by generation of the dialkoxyalkyl radical III produces the desired 2-deoxy-L-ribose triester 4 in excellent overall yield. It has been shown that the similar dialkoxyalkyl radical IV is not an intermediate in the 1,2-acyloxy shift of anomeric radical I.
Jung
M E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA. jung@chem.ucla.edu
Xu
Y
Y
D001089:Arabinose / Q000737:chemistry*; D003855:Deoxyribose / Q000138:chemical synthesis* / Q000737:chemistry
D003855:Deoxyribose; D001089:Arabinose