93752-54-6

Basic information

• Product Name: N-[(1S,5S,6S)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide
• Synonyms: LL-C 10037alpha;N-(4,5-Epoxy-2-hydroxy-3-oxo-1-cyclohexen-6-yl)acetamide;N-(4-Hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl)acetamide
• CAS NO: 93752-54-6
• Molecular Formula: C₈H₉NO₄
• Molecular Weight: 183.1614
• Mol File: 93752-54-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 562.3°C at 760 mmHg
• Flash Point: 293.9°C
• Density: 1.47g/cm³
• Vapor Pressure: 5.48E-15mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: N-[(1S,5S,6S)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S,5S,6S)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide(93752-54-6)
• EPA Substance Registry System: N-[(1S,5S,6S)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide(93752-54-6)

Safety Data

• Hazardous Substances Data: 93752-54-6(Hazardous Substances Data)

Upstream product

• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 
• 69945-45-5 (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene 
• 1560848-58-9 (1S,5S,6R)-3-azido-5-[(tert-butyldimethylsilyl)oxy]-7-oxabicyclo[4.1.0]hept-3-en-2-one 
• 1560848-54-5 (1R,3S,5R,6S,7S)-6-[(tert-butyldimethylsilyl)oxy]-8-[(1R)-1-(4-methoxyphenyl)ethyl]-4-oxa-8-azatricyclo[5.1.0.0^3,5]octan-2-one 
• 1560848-51-2 (1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-7-[(1R)-1-(4-methoxyphenyl)ethyl]-7-azabicyclo[4.1.0]hept-3-en-2-one 
• 1560848-42-1 (1R,5R,6S)-5-[(tert-butyldimethylsilyl)oxy]-7-[(1R)-1-(4-methoxyphenyl)ethyl]-7-azabicyclo[4.1.0]heptan-2-one 
• 627873-21-6 (1aR,3aR,6aS,6bS)-1-(4-Methoxy-benzyl)-5,5-dimethyl-hexahydro-4,6-dioxa-1-aza-cyclopropa[e]inden-2-one 
• 355401-57-9 (3aR,7aS)-6-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-one 
• 179949-73-6 4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclohex-2-enone 
• 121651-99-8 (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 
• 1560848-59-0 N-[(1S,5S,6R)-5-[(tert-butyldimethylsilyl)oxy]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]acetamide 
• 174531-90-9 (2R,4R,7S,8R,9S)-11-<(allyloxycarbonyl)amino>-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-2,4-dimethyl-1,5-dioxaspiro<5.5>non-10-ene 
• 174591-71-0 (2S,3R,4S)-6--4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 
• 174591-70-9 (2S,3R,4S)-6-<(allyloxycarbonyl)amino>-4-(tert-butyldiphenylsilyloxy)-2,3-epoxycyclohex-5-enone 

Relevant articles and documents

Use of aziridines for the stereocontrolled synthesis of (-)-LL-C10037α, (+)-MT35214, and (+)-4-epi-MT35214

Strategies for the synthesis of the title compounds have been developed using a diastereoselective aziridination reaction of 4-O-substituted cyclohexenones. Aziridination using a chiral amine permitted resolution of a 4-hydroxycyclohexane derivative, and this resulted in the synthesis of both enantiomers of the title compound. Alternatively, the chiral 4-hydroxycyclohexenone starting material was derived from quinic acid. In both cases stereoselective epoxidation and opening of the aziridine ring with hydrazoic acid afforded the 2-azidocyclohexenone, which was transformed to the 2-acetamido group present in the natural product.

Enantioselective synthesis of (-)-LL-C10037α from benzoquinone

(formula presented) The enantioselective total synthesis of the Streptomyces metabolite (-)-LL-C10037α has been accomplished in 10 steps and 20% overall yield. An early chiral intermediate was resolved with Candida rugosa lipase to provide (+)-5 with an e

Biosynthesis of Antibiotic LL-C10037α: The Steps beyond 3-Hydroxyanthranilic Acid

The six steps from 3-hydroxyanthranilic acid to the epoxyquinol LL-C10037α, 1, produced by Streptomyces LL-C10037 have been determined by whole-cell feedings with deuterated substrates and by cell-free studies. 3-Hydroxyanthranilic acid, 2, is decarboxylated to 2-hydroxyaniline, 11, and then oxidized to 2,5-dihydroxyaniline, 8.Acetylation at nitrogen and oxidation afford acetamido-1,4-benzoquinone, 4.A crude cell-free preparation has been found to epoxidize 4 to the epoxyquinone 16 in the presence of O2 and either NaDH or NADPH.Reduction of 16 yields 1.Therelationship of this pathway to that of fungi that produce patulin via analogous intermediates from 6-methylsalicylic acid is discussed.