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
• Article Data: 6

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

General Description

Pentenomycin I, also known as (+)-Pentenomycin I, is a tricyclic macrolide antibiotic compound that is obtained from Streptomyces. It is a natural product component that is recognized for its feature of being a non-crystalline, solid substance. PENTENOMYCIN I,(+)- exhibits effective antibacterial activity against several Gram-positive organisms. Due to its structure and biological activity, it serves as a vital compound of interest for medicinal chemistry research. It is usually stored at room temperature in a well-sealed and dry environment to uphold its stability and maintain its functional properties during research applications. As with most chemical compounds, it needs to be handled carefully as it can cause skin and eye irritation following 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

• 132900-78-8 4-(3-Benzenesulfinyl-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 132900-79-9 7-Benzenesulfinyl-9-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.4]nonan-6-one 
• 477842-53-8 4-(1-Hydroxy-3-phenylsulfanyl-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 80963-30-0 t-3-<(tert-butyldimethylsilyl)oxy>-2-hydroxy-r-2-<<(tert-butyldimethylsilyl)oxy>methyl>cyclopentanone 
• 80963-19-5 α-(hydroxymethyl)cyclopentenone ethylene ketal 
• 68882-73-5 cis-2,3-dihydroxy-2-<<(tert-butyldimethylsilyl)oxy>methyl>cyclopentanone 
• 57020-97-0 ethyl 5-oxocyclopent-1-en-1-carboxylate 
• 68882-72-4 2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone 
• 68882-71-3 2-(hydroxymethyl)cyclopent-2-enone 
• 10481-34-2 2-bromo-2-cyclopenten-1-one 
• 68241-78-1 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene 
• 80963-24-2 6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene 
• 85806-60-6 Acetic acid (1S,2S,3aR,4R,7S,7aS)-1-bromo-2-hydroxy-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-4,7-methano-inden-2-ylmethyl ester 
• 86531-71-7 (4RS)-4-t-butyldimethylsilyloxy-2-t-butyldimethylsilyloxymethylcyclopent-2-en-1-one 

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.

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).

Stereocontrolled total synthesis of (±)-pentenomycins I-III, their epimers, and dehydropentenomycin I

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