
%0 Journal Article
%A Mcadam, DP 
%A Perera, AMA 
%A Stick, RV 
%T The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-Dimethylarsinyl-&#946;-D-Riboside, a Naturally Occurring Arsenic-Containing Carbohydrate
%J Australian Journal of Chemistry
%D 1987/11/01
%V 40
%N 11
%P 1901-1908
%K 
%R https://doi.org/10.1071/CH9871901
%U https://www.publish.csiro.au/paper/CH9871901 
%X The synthesis of the title compound, isolated from the brown kelp ( Ecklonia radiata ) or the giant clam (Tridacna maxima), is reported. Glycosidation of 1-O-acetyl-2,3,5-tri- O- benzoyl -&#946;-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol &#946;-D- ribofuranosides. Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C5 of the D-ribose residue. Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C5 in a two-step procedure, and removal of protecting groups provided the natural product. 
