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 -β-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 β-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.
The Small Giant Clam, Tridacna maxima Exhibits Minimal Population Genetic Structure in the Red Sea and Genetic Differentiation From the Gulf of Aden