119067-60-6

Basic information

• Product Name: (R)-2-hexen-5-olide
• CAS NO: 119067-60-6
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.12
• Mol File: 119067-60-6.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (R)-2-hexen-5-olide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hexen-5-olide(119067-60-6)
• EPA Substance Registry System: (R)-2-hexen-5-olide(119067-60-6)

Safety Data

• Hazardous Substances Data: 119067-60-6(Hazardous Substances Data)

Upstream product

• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 1018700-57-6 methyl 3,5-dihydroxyhexanoate 
• 121843-07-0 (4R,6R)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-one 
• 121843-08-1 (4R,6S)-4-hydroxy-6-methyltetrahydropyran-2-one 
• 118992-11-3 (-)-6-(6R)-methyldihydropyr-4-en-2-one 
• 521973-92-2 3,5-dihydroxy-hexanoic acid tert-butyl ester 
• 97037-72-4 (R)-5-hydroxy-3-oxo-hexanoic acid tert-butyl ester 
• 116967-26-1 3,5-dioxoheptenoic acid t-butyl ester 
• 127063-34-7 (3R)-E-N,N-dimethyl-3-trimethylsilylhex-4-enamide 
• 113200-98-9 (4R,5R)-5-((1R)-hydroxyethyl)-4-trimethylsilyldihydrofuran-2-one 
• 100636-39-3 methyl 3-carbonyl-5-hexenoate 
• 121772-41-6 (4R)-4-hydroxy-6-phenylselenomethyltetrahydropyran-2-one 
• 119003-49-5 (3R)-(-)-3-hydroxyhex-5-enoic acid 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 

Downstream Products

• 43112-32-9 (R)-(+)-δ-methyl-δ-valerolactone 
• 736966-24-8 (4R,6R)-6-Methyl-4-phenyl-tetrahydro-pyran-2-one 
• 736966-29-3 (2S,4S)-4-Phenyl-hept-6-en-2-ol 
• 736966-26-0 (2R,4S)-4-Phenyl-hept-6-en-2-ol 
• 1005344-35-3 botryolide B 

Relevant articles and documents

Highly regio- and enantioselective reduction of 3,5-dioxocarboxylates

Only the keto group in position C-5 is reduced in the enzymatic reduction of 3,5-dioxocarboxylates by the alcohol dehydrogenase of Lactobacillusbrevis (LBADH; see scheme). The strategy of nature for manipulating β-keto metabolites inspired the development of a chemoenzymatic approach to virtually enantiopure 3,5-dihydroxycarboxylate building blocks. The crucial enzymatic step can be performed on an attractively large scale.

Concise total synthesis of botryolide B

An efficient total synthesis of botryolide B was achieved in 9 longest linear steps with 22% overall yield via esterification of a carboxylic acid with an alcohol fragment and a ring closing metathesis (RCM) reaction as pivotal steps to construct the macrolactone ring system. Our novel approach for the synthesis of the 2-alkene-1,5-diol fragment was achieved by a ring closing metathesis reaction followed by a reductive opening strategy, whereas the carboxylic acid fragment was accessed from commercially available (R)-(+)-α-hydroxy-γ-butyrolactone in three steps.

Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B

Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.