86531-77-3

Upstream product

• 86531-76-2 (4R)-4-benzyloxy-2-benzyloxymethylcyclopent-2-en-1-one 
• 100-39-0 benzyl bromide 
• 77003-55-5 (7R,8R,9R)-9-benzoyloxy-7,8-dihydroxy-1,4-dithiaspiro<4.5>decane 
• 86531-74-0 (8R)-8-benzoyloxy-6-hydroxymethyl-1,4-dithiaspiro<4.4>non-6-ene 
• 86381-47-7 (3R)-3-benzoyloxy-5-oxo-1-cyclopentene-1-carbaldehyde 5-ethylene dithioacetal 
• 95190-57-1 4-Benzyloxy-2-benzyloxymethyl-cyclopent-2-enone 
• 76420-07-0 4-hydroxy-2-(hydroxymethyl)cyclopent-2-en-1-one 
• 86531-75-1 (8R)-8-benzyloxy-6-benzyloxymethyl-1,4-dithiaspiro<4.4>non-6-ene 

Downstream Products

• 86531-79-5 Benzoic acid (1S,2S)-1,2-dihydroxy-5-oxo-cyclopent-3-enylmethyl ester 
• 95107-01-0 6-O-benzylpentenomycin 
• 95107-01-0 6-O-benzylpentenomycin 
• 95190-60-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,5R)-5-benzyloxymethyl-5-hydroxy-4-oxo-cyclopent-2-enyl ester 
• 95107-05-4 6-O-benzyl-4-O-<(αS)-α-methoxy-α-trifluoromethyl-α-phenylacetyl>pentenomycin 
• 86531-80-8 Benzoic acid (1S,5S)-1-hydroxy-2-oxo-5-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-cyclopent-3-enylmethyl ester 
• 95107-02-1 6-O-benzyl-4,5-O-isopropylidenepentenomycin 
• 49644-25-9 (-)-pentenomycin 

Relevant academic research and scientific papers

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.