130508-79-1

Upstream product

• 141782-37-8 (2'R,3'R,5Z)-5-(4'-benzyloxy-2',3'-dihydroxybutylidene)-3-(p-methoxybenzyl)hydantoin 
• 81801-09-4 4-O-benzyl-2,3-O-isopropylidene-D-threose 
• 129829-32-9 5-Z-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin 
• 129744-26-9 N-acetyl N-methoxybenzylhydantoin 

Relevant academic research and scientific papers

Deoxyhydantocidin: Synthesis by base-catalyzed spiro, cyclization and interconversion with the 1'-epimer

Syntheses of the spiro nucleosides 2'-deoxyhydantocidin 3a and its 1'- epimer 3b are described. The newly developed route involves a Horner- Wadsworth-Emmons condensation of the phosphonate 16 with the erythrose derivative 15 affording a mixture of six isomers which was fully assigned by NMR spectroscopy. The mixture was directly converted into the final compounds in an efficient base-catalyzed cylization reaction. A base-catalyzed interconversion between the two isomers was observed.

A new short synthesis of deoxyhydantocidin derivatives

Using erythronolactol 8 as chiral C4 synthon, a new short synthetic pathway was developed to obtain two hydantoin 2'-deoxyribonucleoside epimer derivatives 15a and 15b.