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Synthesis of 1‐ O ‐R‐5‐deoxy‐β‐ D ‐ribofuranosides with (CH 3 ) 2 As and (CH 3 ) 2 AsO as substituents at the 5‐position and a methyl or 2′,3′‐dihydroxypropyl group as the aglycone in the 1‐position
Author(s) -
Liu Jinggao,
O'Brien Daniel H.,
Irgolic Kurt J.
Publication year - 1996
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199602)10:1<1::aid-aoc466>3.0.co;2-a
Subject(s) - chemistry , aglycone , arsine , stereochemistry , arsenic , bromine , total synthesis , natural product , medicinal chemistry , organic chemistry , glycoside , catalysis , phosphine
Six arsenic‐containing β‐ D ‐ribofuranosides, including the naturally occurring (2′R)‐dimethyl[1‐ O ‐(2′,3′‐dihydroxypropyl)‐5‐deoxy‐β‐ D ‐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 three‐carbon 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.