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Synthesis of 1-O-R-5-deoxy-β-D-ribofuranosides with (CH3)2As and (CH3)2AsO as substituents at the 5-position and a methyl or 2′,3′-dihydroxypropyl group as the aglycone in the 1-position

✍ Scribed by Jinggao Liu; Daniel H. O'Brien; Kurt J. Irgolic

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
896 KB
Volume
10
Category
Article
ISSN
0268-2605

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✦ Synopsis

including the naturally occurring (2'R)dimethyl[ l-O-(2',3'-dihydroxypropyl)-5-deoxy-~-~-ribofuranos-5-yl]arsine oxide, were prepared in multi-step reactions from D-ribose and tetramethyldiarsine. The synthetic procedure uses the early substitution of the hydroxy group with bromine at C5, subsequent attachment of a chiral threecarbon aglycone at C1, and final delivery of arsenic at C5. The synthesis provides a viable route for the preparation of multigram quantities of the natural product. Keywords: arsenic-containing ribofuranosides; arsenosugars; (2'R)-dimethyl[l-O-(2',3'-dihydroxypropyl) -5deoxy -P -Dribofuranos -5yllarsine oxide OH, OP(OH)O,CH2CH(OH)CH2OH EXPERIMENTAL Materials Cacodylic acid (commercial herbicide, 515 g I-') was obtained from Vineland Chemical Co. Inc., Vineland, NJ, USA. D-Ribose (99%), p -CCC 0268-2605/96/01000l-l 1

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