THE PREPARATION OF D-RIBOSE-1-C14, D-ARABINOSE-1-C14, AND D-2-DEOXYRIBOSE-1-C14 | Zendy

Desmond H. Murray | Zendy; G. C. Butler | Zendy

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THE PREPARATION OF D-RIBOSE-1-C¹⁴, D-ARABINOSE-1-C¹⁴, AND D-2-DEOXYRIBOSE-1-C¹⁴

Author(s) -

Desmond H. Murray,

G. C. Butler

Publication year - 1959

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v59-257

Subject(s) - chemistry , deoxyribose , yield (engineering) , arabinose , solvent , stereochemistry , cellulose , ribose , organic chemistry , fermentation , xylose , nucleic acid , biochemistry , enzyme , materials science , metallurgy

D-Ribose-1-C 14 and D-arabinose-1-C 14 have been synthesized by a modified Sowden–Fischer procedure in which the mixed sodium nitropentitols resulting from the condensation of erythrose and C 14 H 3 NO 2 have been submitted to a Nef reaction. The epimeric labelled pentoses were isolated by cellulose column chromatography in an over-all radiochemical yield of 19%.Mixed nitropentitols-1-C 14 have been acetylated, partially deacetylated with sodium bicarbonate in a non-polar solvent, and hydrogenated to yield triacetoxy-1-nitropentane-1-C 14 . The mixture of this material and the accompanying undeacetylated nitropentitols gave rise, via a Nef reaction, to D-2-deoxyribose-1-C 14 (6.3%), D-ribose-1-C 14 (3.1%), and D-arabinose-1-C 14 (2.9%).

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