115265-81-1

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 

Downstream Products

• 138328-70-8 (2'S)-2',3'-dihydroxypropyl tri-O-benzoyl-β-D-ribofuranoside 
• 138328-71-9 (2'R)-3'-bromo-2'-hydroxypropyl tri-O-benzoyl-β-D-ribofuranoside 

Relevant academic research and scientific papers

The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-dimethylarsinyl-β-D-riboside, a Naturally Occurring Arsenic-Containing Carbohydrate

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 C 5 of the D-ribose residue.Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C 5 in a two-step procedure, and removal of protecting groups provided the natural product.