130607-26-0

Usage

Uses

Used in Pharmaceutical Industry:
Hydantocidin is used as a pharmaceutical compound for its selective inhibition of plant adenylsuccinate synthetase. This property makes it a potential candidate for the development of new drugs targeting specific plant enzymes, which could have applications in agriculture or other related fields.
Used in Research and Development:
Hydantocidin is used as a research tool for studying the structure and function of adenylsuccinate synthetase and its role in plant metabolism. Understanding the interaction between hydantocidin and this enzyme can provide valuable insights into the development of new drugs and therapies.
Used in Crop Protection:
Hydantocidin's ability to selectively inhibit plant adenylsuccinate synthetase could be utilized in the development of crop protection agents. By targeting specific plant enzymes, it may be possible to create compounds that protect crops from pests or diseases without harming the crop itself.
Used in Plant Metabolism Studies:
Hydantocidin can be used as a research tool to study plant metabolism and the role of adenylsuccinate synthetase in various metabolic pathways. This can help researchers better understand plant growth, development, and response to environmental stressors.

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 
• 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 
• 130607-24-8 <2R,3S,4R,5S>-2-Benzyloxymethyl-3,4-dihydroxy-1-oxa-6,8-diazaspiro<4.4>nonane-7,9-dione 
• 130509-14-7 [5S-(5α,7α,8β,9β)]-1,3-diaza-7-hydroxymethyl-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione 
• 158227-09-9 C₂₈H₂₂N₂O₉ 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 339540-26-0 2,5-anhydro-6-O-benzyl-1,1-dichloro-1-deoxy-3,4-O-isopropylidene-D-ribo-hex-1-enitol 
• 339540-27-1 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-α-D-ribo-hexofuranosonate 
• 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 
• 392743-23-6 [5S-(5α,7α,8β,9β)]-8,9-isopropylidenedioxy-7-[4-(methoxybenzyloxy)methyl]-6-oxa-2-thioxo-1,3-diazaspiro[4.4]nonan-4-one 
• 339540-28-2 methyl 2,5-anhydro-2-azido-6-O-benzyl-3,4-O-isopropylidene-β-D-ribo-hexulofuranosonate 

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.

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.

Natural Products as Pesticides: Two Examples of Stereoselective Synthesis

The strategy and synthetic efforts leading to efficient stereoselective syntheses of thiangazole, a tris-thiazolinyl-oxazole metabolite isolated from Polyangium spp., and hydantocidin, a spironucleoside metabolite isolated from Streptomyces hygroscopicus, are discussed.

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.

Synthesis of 5-epiHydantocidin from D-Ribose

Tetra-n-propyl ammonium perruthenate in the presence of morpholin-N-oxide induced the unanticipated transformation of the epimeric α-azido-1,4-lactones 4 into the bicyclic amine 3 and provided the key step in the synthesis of 5-epihydantocidin 2.Brief investigations into the acid catalysed equilibration of hydantocidin 1 and 5-epihydantocidin 2 are described.

PSICOFURANOSE AND PSICOPYRANOSE DERIVATIVES

D-psicofuranose and D-psicopyranose derivatives represented by general formulae (I) and (II), useful as the key intermediates in a novel process for producing hydantocidin; wherein R1 through R8 may be the same or different from one another and each represents hydrogen or a hydroxyl-protecting group; and X represents optionally protected hydroxymethyl, carboxyl, carbamoyl or allophanoyl.

Stereoselective bromination of β-ribofuranosyl amide. Enantioselective synthesis of (+)-hydantocidin

The synthesis of hydantocidin, a potent herbicidal natural product, is highlighted by a stereoselective bromination of β-D-ribofuranosyl amide to give only the α-bromo β-amide and subsequent spirocyclization about the anomeric position with silver cyanate to form the hydantoin moiety.

Stereoselectivity synthesis of (+)-hydantocidin

The naturally occurring spironuceleoside (+)-hydantocidin 1 was synthesized from 1,2:3,4-di-O-isopropylidene-D-psicofuranose using a new oxygen-bridged intramolecular Vorbruggen coupling of the N-hydroxyurea 5 in presence of a catalytic amount of trimethylsilytriflate.

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.