133908-91-5

Upstream product

• 133886-01-8 2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose 
• 133886-05-2 1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose 
• 133886-06-3 1-β-Azido-1-dehydro-1-α-carbamoyl-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 
• 100-39-0 benzyl bromide 
• 339540-29-3 methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-[3-N-(4-methoxybenzyl)ureido]-β-D-ribo-2-hexulofuranosonate 
• 503610-48-8 methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-[3-N-(4-methoxybenzyl)ureido]-α-D-ribo-2-hexulofuranosonate 
• 339540-28-2 methyl 2,5-anhydro-2-azido-6-O-benzyl-3,4-O-isopropylidene-β-D-ribo-hexulofuranosonate 
• 503610-46-6 methyl 2,5-anhydro-2-azido-6-O-benzyl-3,4-O-isopropylidene-α-D-ribo-hexulofuranosonate 
• 145121-83-1 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxa-2-thioxo-spiro[4.4]nonan-4-one 
• 392743-12-3 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-β-D-ribo-hexofuranosonate 
• 339540-27-1 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-α-D-ribo-hexofuranosonate 
• 339540-26-0 2,5-anhydro-6-O-benzyl-1,1-dichloro-1-deoxy-3,4-O-isopropylidene-D-ribo-hex-1-enitol 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 

Relevant academic research and scientific papers

Syntheses of hydantocidin and C-2-thioxohydantocidin

Hydantocidin (12), a naturally occurring strong herbicide, was synthesized in 35.2% overall yield, with accompanying 5-epi-hydantocidin (12′) in 9.6% overall yield via isothiocyanate (13) and spiro-hydantoin (10) from 2,3-O-isopropylidene-D-ribono-1,4-lactone (1). C-2-Thioxo-hydantocidin (24) was also synthesized in 16.5% overall yield with accompanying 5-epi-C-2-thioxohydantocidin (24′, 9.2% yield) via isothiocyanate (22).

Synthesis of hydantocidin and C-2-thioxo-hydantocidin

Hydantocidin, a naturally occurring strong herbicide, was synthesized in an overall yield of 35.2%, with the accompanying 1′-epi-hydantocidin in overall 9.6% yield from 2,3-O-isopropylidene-D-ribono-1,4-lactone. C-2-thioxo-hydantocidin and its spiro-epimer were also synthesized in an overall yield of 14.4% and 8.5%, respectively.

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.