153289-41-9

Upstream product

• 153289-40-8 benzyl 6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranoside 
• 161939-00-0 (3aR,4S,6R,6aR)-4-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 

Downstream Products

• 153289-42-0 benzyl 5-O-benzyl-1-carbamoyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside 
• 153289-44-2 benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-β-D-ribofuranoside 
• 153289-43-1 benzyl 1-allophanoyl-5-O-benzyl-1-dehydro-2,3-O-isopropylidene-β-D-ribofuranoside 
• 130607-26-0 [5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione 

Relevant academic research and scientific papers

Novel synthesis of (+)-hydantocidin based on the plausible biosynthetic pathway

The title synthesis was examined by employing two synthetic schemes which feature N,O-spiroketal formation as a key step. Although the stepwise synthesis starting with D-fructose and proceeding through the D-psicose derivatives successfully produced a mixture of (+)-hydantocidin (1) and its C5-epimer [(-)-5-epihydantocidin (2)], the one-step synthesis utilizing D-isoascorbic acid and urea as starting materials was found to give 2 more selectively than 1. Studies on the key N,O-spiroketal formation and epimerization between 1 and 2 were also carried out to explore some novel aspects of the obtained results.

A novel biogenetic type synthesis of (+)-hydantocidin

The title synthesis was accomplished by featuring the proposed biosynthetic pathway. The synthesis commenced with the D-psicose derivative readily obtainable from D-fructose and employed intramolecular N, O-spiroketal formation of the open-chain N-acylurea derivative as a key step.