68907-79-9

Basic information

• Product Name: PENTENOMYCIN I,(+)-
• Synonyms: PENTENOMYCIN I,(+)-
• CAS NO: 68907-79-9
• Molecular Formula: C6H8O4
• Molecular Weight: 144.13
• Mol File: 68907-79-9.mol

Chemical Properties

• Boiling Point: 349.2 °C at 760 mmHg
• Flash Point: 179.2 °C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 2.89E-06mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: PENTENOMYCIN I,(+)-(CAS DataBase Reference)
• NIST Chemistry Reference: PENTENOMYCIN I,(+)-(68907-79-9)
• EPA Substance Registry System: PENTENOMYCIN I,(+)-(68907-79-9)

Safety Data

• Hazardous Substances Data: 68907-79-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PENTENOMYCIN I,(+)is used as an antibiotic for its potent antibacterial activity against several Gram-positive organisms. Its effectiveness in combating bacterial infections makes it a valuable compound in the development of new antimicrobial drugs.
Used in Medicinal Chemistry Research:
PENTENOMYCIN I,(+)is used as a research compound for studying its structure and biological activity. Its unique properties and potential applications in medicine make it an important subject for further investigation and exploration in the field of medicinal chemistry.
Used in Drug Development:
PENTENOMYCIN I,(+)is used as a lead compound in the development of new drugs. Its potent antibacterial properties and potential for further modification and optimization make it a promising candidate for the creation of novel therapeutic agents.
Storage and Handling:
PENTENOMYCIN I,(+)is used as a stable compound when stored at room temperature in a well-sealed and dry environment. Proper storage is essential to maintain its stability and functional properties during research applications. Additionally, it is important to handle PENTENOMYCIN I,(+)with care, as it can cause skin and eye irritation upon exposure.

InChI:InChI=1/C6H8O4/c7-3-6(10)4(8)1-2-5(6)9/h1-2,4,7-8,10H,3H2

Upstream product

• 124325-96-8 (5S,9S)-9-Hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.4]non-7-en-6-one 
• 68882-74-6 cis-4,5-dihydroxy-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone 
• 80963-32-2 t-4-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-r-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone 
• 85806-62-8 Acetic acid (1R,2R,3aR,4R,7S,7aS)-2-acetoxymethyl-2-hydroxy-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-1-yl ester 
• 86531-71-7 (4RS)-4-t-butyldimethylsilyloxy-2-t-butyldimethylsilyloxymethylcyclopent-2-en-1-one 
• 80963-24-2 6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene 
• 68241-78-1 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene 
• 68882-71-3 2-(hydroxymethyl)cyclopent-2-enone 
• 57020-97-0 ethyl 5-oxocyclopent-1-en-1-carboxylate 
• 68882-73-5 cis-2,3-dihydroxy-2-<<(tert-butyldimethylsilyl)oxy>methyl>cyclopentanone 
• 80963-30-0 t-3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-r-2-<<(tert-butyldimethylsilyl)oxy>methyl>cyclopentanone 
• 132900-79-9 7-Benzenesulfinyl-9-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.4]nonan-6-one 
• 132900-78-8 4-(3-Benzenesulfinyl-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 477842-53-8 4-(1-Hydroxy-3-phenylsulfanyl-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of (±)-pentenomycin

A concise stereoselective route to (±)-pentenomycin 1 in 33% overall yield starting from the readily accessible Diels-Alder adduct 4 is reported. The key reaction involves decarbonylation of β-methoxy-α,β-unsaturated aldehyde 8 obtained from β-hydroxy-dimethylketal 6.

Intramolecular acylation of α-sulfinyl carbanion: A facile synthesis of (±)-pentenomycin I and (±)-epipentenomycin I

(±)-Pentenomycin I and (±)-epipentenomycin I were synthesized, starting from methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate. The key reaction involved the intramolecular acylation of α-sulfinyl carbanion and pyrolysis of the resulting product.

Studies Related to Cyclopentanoid Natural Products. Part 3. Synthesis of Pentenomycin and its Racemate

(4R)-4-Benzyloxy-2-benzyloxymethylcyclopent-2-en-1-one (9b) reacted with osmium(VIII) oxide to give (2S,3S,4R)-4-benzyloxy-2-benzyloxymethyl-2,3-dihydroxycyclopentan-1-one (8b), the cis-hydroxylation occurring anti to the 4-benzyloxy group.By a hydrogenolysis-dehydration sequence, compound (8b) was converted into pentenomycin (1a).Although the optical rotations of the synthetic pentenomycin (1a) and its 4,5,6-tri-O-acetyl, 2-bromo-4,5,6-tri-O-acetyl, and 6-O-benzyl derivatives (13a), (13b), and (1d), were substantially different from those reported in the literature, the compounds were shown to be enantiomerically pure.When treated with t-butyldimethylsilyl chloride, (8R)-8-hydroxy-6-hydroxymethyl-1,4-thiaspiro-non-6-ene (10b) was converted into its disilyl ether (10f).The last-cited compound reacted with benzeneseleninic anhydride to give (4R)-4-t-butyldimethylsilyloxy-2-t-butyldimethylsilyloxymethylcyclopent-2-en-1-one (9d), which was converted into pentenomycin (1a) by sequential reactions involving osmium(VIII) oxide and hydrochloric acid.The racemate of compound (9d), prepared from the racemate of 4-hydroxy-2-hydroxymethylcyclopent-2-en-1-one (9c) by reaction with t-butyldimethylsilyl chloride, was similarly transformed into the racemate of pentenomycin (1a).

Syntheses of (±)-and (-)-pentenomycin I

Syntheses of the cyclopentanoid antibiotic. (-)-pentenomycin I, from D-(-)-quinic acid are described; (±)-pentenomycin I is also prepared from 3-hydroxymethyl-2-methylfuran.