145121-83-1

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 

Downstream Products

• 133908-91-5 [5R-(5α,7β,8α,9α)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione 
• 130607-26-0 [5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione 
• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 

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.