130607-26-0

Basic information

• Product Name: hydantocidin
• Synonyms: hydantocidin;(+)-Hidantocidin;(2S)-4,5-Dihydro-3α,4α-dihydroxy-5β-(hydroxymethyl)spiro[furan-2(3H),4'-imidazolidine]-2',5'-dione;(4S)-3'α,4'α-Dihydroxy-5'β-(hydroxymethyl)-4',5'-dihydrospiro[imidazolidine-4,2'(3'H)-furan]-2,5-dione
• CAS NO: 130607-26-0
• Molecular Formula: C7H10N2O6
• Molecular Weight: 218.164
• Mol File: 130607-26-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 358.84°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.5295 (rough estimate)
• Refractive Index: 1.4880 (estimate)
• CAS DataBase Reference: hydantocidin(CAS DataBase Reference)
• NIST Chemistry Reference: hydantocidin(130607-26-0)
• EPA Substance Registry System: hydantocidin(130607-26-0)

Safety Data

• Hazardous Substances Data: 130607-26-0(Hazardous Substances Data)

Usage

Description

Hydantocidin (52), a microbial spironucleoside, selectively inhibits plant adenylsuccinate synthetase only after in vivo phosphorylation, resulting in the 5 -monophosphate 52, an analog of adenosine 5 -monophosphate (74) .

InChI:InChI=1/C7H10N2O6/c10-1-2-3(11)4(12)7(15-2)5(13)8-6(14)9-7/h2-4,10-12H,1H2,(H2,8,9,13,14)/t2-,3-,4-,7+/m1/s1

Upstream product

• 130607-25-9 [5R-(5α,7β,8α,9α)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione 
• 89-65-6 isoascorbic acid 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 133909-09-8 (2R,3S,4R,5S)-2-benzyloxymethyl-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione 
• 158227-09-9 C₂₈H₂₂N₂O₉ 
• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 130607-24-8 <2R,3S,4R,5S>-2-Benzyloxymethyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4.4>nonane-7,9-dione 
• 133909-08-7 (2R,3S,4R,5S)-2-benzyloxymethyl-8-(4-methoxybenzyl)-6-benzyloxycarbonyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4,4>nonane-7,9-dione 
• 133909-07-6 (2R,5S)-2-benzyloxymethyl-8-(4-methoxybenzyl)-6-benzyloxycarbonyl-1-oxa-6,8-diazaspiro<4,4>nonane-3-ene-7,9-dione 
• 129829-32-9 5-Z-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin 
• 129744-27-0 5-E-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin 
• 132490-40-5 (2S,5S)-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 
• 129744-34-9 5-<(2R,3R)-4-benzyloxy-2,3-epoxy-1-t-butyldimethylsilyloxy>butyl-3-(4-methoxybenzyl)hydantoin 

Relevant articles and documents

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).

One-step synthesis of (-)-5-epi-hydantocidin

One-step synthesis of (-)-5-epi-hydantocidin was achieved by heating a mixture of D-isoascorbic acid and urea without solvent. Studies on N,O-spiroketal formation and epimerization between (+)-hydantocidin and (-)-5-epi-hydantocidin were also carried out to explore some mechanistic aspects of the obtained results.

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.