240118-48-3

Basic information

• Product Name: D-erythro-Pentaric acid, 2,3-dideoxy-3-methyl-4-C-methyl-, 1,4-lactone (9CI)
• Synonyms: D-erythro-Pentaric acid, 2,3-dideoxy-3-methyl-4-C-methyl-, 1,4-lactone (9CI)
• CAS NO: 240118-48-3
• Molecular Formula: C7H10O4
• Molecular Weight: 158.1519
• Product Categories: CARBOXYLICACID
• Mol File: 240118-48-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-erythro-Pentaric acid, 2,3-dideoxy-3-methyl-4-C-methyl-, 1,4-lactone (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: D-erythro-Pentaric acid, 2,3-dideoxy-3-methyl-4-C-methyl-, 1,4-lactone (9CI)(240118-48-3)
• EPA Substance Registry System: D-erythro-Pentaric acid, 2,3-dideoxy-3-methyl-4-C-methyl-, 1,4-lactone (9CI)(240118-48-3)

Safety Data

• Hazardous Substances Data: 240118-48-3(Hazardous Substances Data)

Upstream product

• 49620-10-2 (+)-trans-β-methyl-γ-carboxy-γ-valerolactone 
• 60375-12-4 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid methyl ester 
• 76405-08-8 2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carbonitrile 
• 74-90-8 hydrogen cyanide 
• 6628-79-1 3-methyllevulinic acid 
• 55424-74-3 ethyl 3-methyl-4-oxopentanoate 
• 1037551-27-1 C₉H₁₆O 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 863423-71-6 (4R)-4-[1,3]dithian-2-ylidene-3-methylpentanoic acid diethylamide 
• 863423-72-7 (4R,5R)-5-(2-methoxy-[1,3]dithian-2-yl)-4,5-dimethyldihydrofuran-2-one 
• 863423-69-2 (3R)-4-diethylcarbamoyl-2,3-dimethylbutyric acid methyl ester 
• 863423-70-5 (3R)-2,3-dimethylpentanedioic acid 1-methyl ester 
• 151-50-8 potassium cyanide 
• 86577-63-1 (2R,3R)-5-Methoxy-2,3-dimethyl-tetrahydro-furan-2-carboxylic acid methyl ester 

Downstream Products

• 60660-35-7 (2R-trans)-tetrahydro-2,3-dimethyl-5-oxo-2-furancarboxylic acid 

Relevant articles and documents

Genus Crotalaria 13. Crobarbatine, a new pyrrolizidine alkaloid of C. barbata R.

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Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid

Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea-H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

Oxidative cyclizations and the synthesis of lactones: A streamlined synthesis of epi-crobarbatic acid

While anodic cyclizations have been shown to be compatible with the synthesis of lactones, the previous synthetic route to the starting materials was cumbersome and limited the overall utility of the approach. In this manuscript, a new strategy is reported that allows for very rapid synthesis of the electrolysis substrates. In addition, an efficient conversion of the ortho ester product obtained from the oxidative cyclization to a lactone acid is reported. The result is a dramatically improved synthetic strategy for the synthesis of functionalized tetrahydrofuranones.