130607-23-7

Upstream product

• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 130607-21-5 <2R,3S,4R,5R>-2-Benzyloxymethyl-8-(4-methoxybenzyl)-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4.4>nonane-7,9-dione 
• 138457-70-2 1-Amino-1-carbamoyl-1-dehydro-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose 
• 133886-04-1 2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose 
• 133886-06-3 1-β-Azido-1-dehydro-1-α-carbamoyl-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose 
• 133886-05-2 1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose 
• 132490-41-6 (2S,5R)-2-benzyloxymethyl-8-(4-methoxybenzyl)-1-oxa-6,8-diazaspiro<4,4>nonane-3-ene-7,9-dione 
• 133886-01-8 2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose 

Relevant academic research and scientific papers

SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (4): SYNTHESIS OF STEREOSISOMERS OF (+)-HYDANTOCIDIN

The stereoisomers of (+)-hydantocidin were synthesized by diastereoselective dihydroxylation directly or epoxidation followed by ring opening of 1-oxa-6,8-diazaspirononane-3-ene-7,9-dione systems.

Synthetic studies on (+)-hydantocidin (3): A new synthetic method for construction of the spiro-hydantoin ring at the anomeric position of D-ribofuranose

A facile synthetic route for the large-scale preparation of a herbicidal natural product, (+)-hydantocidin is described. The protected D-psicose 6, prepared in five steps from D-fructose, was stereospecifically converted to azido-amide 14 by N-glycosidation (TMSN3/TMSOTf), oxidation and animation. Hydantoin ring-construction on 14 was achieved by aza-Wittig reaction (PBu3/CO2/CH3CN) to give 16 without epimerization at the anomeric center. After acetylation, stepwise deprotection of 24 afforded (+)-hydantocidin 1 in 16% overall yield from D-fructose.