61262-92-8

Basic information

• Product Name: (5S)-5-Acetyltetrahydrofuran-2-one
• Synonyms: (5S)-5-Acetyltetrahydrofuran-2-one
• CAS NO: 61262-92-8
• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.13
• Mol File: 61262-92-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5S)-5-Acetyltetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-Acetyltetrahydrofuran-2-one(61262-92-8)
• EPA Substance Registry System: (5S)-5-Acetyltetrahydrofuran-2-one(61262-92-8)

Safety Data

• Hazardous Substances Data: 61262-92-8(Hazardous Substances Data)

Upstream product

• 54848-33-8 (S)-tetrahydro-5-oxo-2-furancarbonyl chloride 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 89158-13-4 (S)-(-)-γ-diazoacetyl-γ-butyrolacetone 
• 75-16-1 methylmagnesium bromide 
• 74-83-9 methyl bromide 
• 56-86-0 L-glutamic acid 

Downstream Products

• 81694-52-2 (S)-5-(2-Chloro-1-methyl-1-phenylselanyl-ethyl)-dihydro-furan-2-one 
• 35903-48-1 2,3,6-tri-deoxy-L-threo-hexose 
• 27518-97-4 D-(+)-amicetose 

Relevant articles and documents

Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products

Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.

SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID

L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.