New and convenient synthesis of 2-deoxy-D-ribose from 2,4-O-ethylidene-D-erythrose

Journal Article · Mon Jan 01 04:00:00 UTC 1979 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01328a029· OSTI ID:5890959

Hauske, J R; Rapoport, H

A new synthesis is described of 2-deoxy-D-erythro-pentose (2-deoxy-D-ribose,2-deoxy-D-arabinose (1)), starting from D-glucose. The synthesis proceeds through direct olefination of 2,4-O-ethylidene-D-erythrose (2) by addition of the stabilized ylides generated from dimethylphosphorylmethyl phenyl sulfide (4) and the corresponding sulfoxide 5. These afford the key intermediates, thio-enol ether 7 and ..cap alpha..,..beta..-unsaturated sulfoxide 8, which when subjected to mercuric ion assisted hydrolysis gave high yields of 2-deoxy-D-ribose (1). This facile chain extension of 2 required its existance as a monomer, and conditions effective for obtaining the monomer have been developed. Detailed /sup 1/H and /sup 13/C NMR studies of these compounds are presented.

• Research Organization: Univ. of California, Berkeley
• OSTI ID: 5890959
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 44:14; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
ALDEHYDES
CARBOHYDRATES
CARBON 13
CARBON ISOTOPES
CHEMICAL PREPARATION
DEOXYRIBOSE
ELEMENTS
EVEN-ODD NUCLEI
HYDROGEN
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MONOSACCHARIDES
NONMETALS
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ORGANIC COMPOUNDS
PENTOSES
RESONANCE
SACCHARIDES
STABLE ISOTOPES
SYNTHESIS