510-18-9

Basic information

• Product Name: acetomycin
• Synonyms: acetomycin;3-Acetyl-5-(acetyloxy)-3,4-dimethyltetrahydrofuran-2-one;3-Acetyl-5-acetoxy-4,5-dihydro-3,4-dimethyl-2(3H)-furanone;(3S,4S,5R)-3-Acetyl-5-(acetyloxy)dihydro-3,4-dimethyl-2(3H)-furanone;NSC 350598
• CAS NO: 510-18-9
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.22
• Mol File: 510-18-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 115-116℃ (methanol )
• Boiling Point: 336.2°Cat760mmHg
• Flash Point: 148.9°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: acetomycin(CAS DataBase Reference)
• NIST Chemistry Reference: acetomycin(510-18-9)
• EPA Substance Registry System: acetomycin(510-18-9)

Safety Data

• Hazardous Substances Data: 510-18-9(Hazardous Substances Data)

Usage

Uses

Acetomycin is an anti-biotic, anti-fungal, anti-protozoal, and anti-bacterial agent.

InChI:InChI=1/C10H14O5/c1-5-8(14-7(3)12)15-9(13)10(5,4)6(2)11/h5,8H,1-4H3/t5-,8-,10+/m1/s1

Upstream product

• 103560-91-4 (2S,3S,4R)-4-acetoxy-4-hydroxy-2-<(1R)-1-hydroxyethyl>-2,3-dimethylbutanoic acid γ-lactone 
• 155224-35-4 (3S,4S,5R)-3,5-Diacetyl-3,4-dimethyl-dihydro-furan-2-one 
• 208172-57-0 (3R)(4S)(5R)-5-acetoxy-3-acetyl-3-(1,3-dithianyl)-4-methyl-dihydro-2(3H)-furanone 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 635317-44-1 (3S,4S,5S)-5-Hydroxy-3,4-dimethyl-3-(2-methyl-[1,3]dioxolan-2-yl)-dihydro-furan-2-one 
• 635317-41-8 (E)-(2S,3R)-2-Acetyl-2,3-dimethyl-5-phenyl-pent-4-enoic acid methyl ester 
• 635317-42-9 (E)-(2S,3R)-2,3-Dimethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-5-phenyl-pent-4-enoic acid 
• 40834-42-2 5-hydroxy-4-methyl-5H-furan-2-one 
• 155224-28-5 (-)-(4S)(5R)-5-acetoxy-4-methyl-dihydro-2(3H)-furanone 
• 180063-09-6 (-)-5-(R)-acetoxy-4-methyl-2(5H)-furanone 
• 155224-33-2 (3S,4S,5R)-5-((S)-1-Hydroxy-ethyl)-3-isopropenyl-3,4-dimethyl-dihydro-furan-2-one 
• 155224-34-3 (3S,4S,5R)-5-Acetyl-3-isopropenyl-3,4-dimethyl-dihydro-furan-2-one 
• 155224-30-9 (3R,4S,5R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropenyl-4-methyl-dihydro-furan-2-one 
• 155224-31-0 (4S,5R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylidene-4-methyl-dihydro-furan-2-one 

Downstream Products

• 1121-05-7 2,3-dimethylcyclopent-2-enone 

Relevant articles and documents

Asymmetric synthesis of acetomycin

The synthesis of (-)-acetomycin 1, a highly functionalized γ-lactone with antitumor activity, was achieved in five steps with nearly complete enantioselectivity. The key step was realized by a large scale lipase R catalyzed esterification of 5-hydroxy-4-methyl-2(5H)-furanone 2 providing (- )-(5R)-5-acetoxy-4-methyl-2(5H)-furanone 3 with an e.e. of 99%.

Total synthesis of (+/-)-acetomycin and design of esterase-resistant analogs.

The synthesis of acetomycin and related analogs was investigated. Acetomycin was synthesized from diethyl allyl(methyl)malonate in 6.5% yield over 18 steps. The total number of steps was improved compared to our previous synthesis; i.e., four steps shorte

A Selective Baeyer-Villiger Oxidation: A Total Synthesis of (-)-Acetomycin

A short, stereoselective synthesis of (-)-acetomycin (2) from L-threonine is reported.The final step in the synthesis is a selective Baeyer-Villiger oxidation that discriminates between two methyl ketones.