147659-07-2

Basic information

• Product Name: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4R,5S,6R)-(9CI)
• Synonyms: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4R,5S,6R)-(9CI)
• CAS NO: 147659-07-2
• Molecular Formula: C9H16O3
• Molecular Weight: 172.22
• Product Categories: ISOPROPYL
• Mol File: 147659-07-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 90-92 °C
• Boiling Point: 299.6±23.0 °C(Predicted)
• Appearance: /
• Density: 1.056±0.06 g/cm3(Predicted)
• PKA: 13.51±0.60(Predicted)
• CAS DataBase Reference: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4R,5S,6R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4R,5S,6R)-(9CI)(147659-07-2)
• EPA Substance Registry System: 2H-Pyran-2-one,tetrahydro-4-hydroxy-5-methyl-6-(1-methylethyl)-,(4R,5S,6R)-(9CI)(147659-07-2)

Safety Data

• Hazardous Substances Data: 147659-07-2(Hazardous Substances Data)

Upstream product

• 795279-41-3 (4S,5R)-5-hydroxy-4,6-dimethyl-3-oxoheptanoic acid methyl ester 
• 115560-90-2 (2R)-(E)-1-(phenylmethoxy)-4-hexen-2-ol 
• 238757-51-2 (1S,5R,6S,7S,8S)-7-Benzyloxy-6,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonan-3-one 
• 61230-54-4 (R)-1-((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 
• 21665-16-7 O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose 
• 141-78-6 ethyl acetate 
• 63522-23-6 3-desoxy-1,2-O-isopropylidene-3-C-methylidene-α-D-erythro-pentodialdo-1,4-furanose 
• 174420-16-7 (2S,3R,4S,5R)-5-isopropyl-4-methyl-tetrahydrofuran-2,3-diol 
• 96918-55-7 1-((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanone 
• 1312341-56-2 (R)-methyl 3-hydroxy-3-((1R,2S)-2-isopropylcyclopropyl)propanoate 
• 1312341-55-1 (R)-4-benzyl-3-((R)-3-hydroxy-3-((1R,2S)-2-isopropylcyclopropyl)propanoyl)-5,5-dimethyloxazolidin-2-one 
• 1312341-54-0 (R)-4-benzyl-3-((2R,3S)-2-chloro-3-hydroxy-3-((1R,2S)-2-isopropylcyclopropyl)propanoyl)-5,5-dimethyloxazolidin-2-one 
• 1312341-53-9 (R)-4-benzyl-3-((2R,3S,E)-2-chloro-3-hydroxy-6-methylhept-4-enoyl)-5,5-dimethyloxazolidin-2-one 
• 224580-62-5 (4S,5R)-3-<(2'R,3'R)-3'-<(tert-Butyldimethylsilyl)oxy>-2',4'-dimethylpentanoyl>-4-methyl-5-phenyloxazolidin-2-one 

Downstream Products

• 128683-72-7 (+)-5(S)-methyl-6(R)-isopropyl-5,6-dihydro-pyran-2-one 

Relevant articles and documents

Total syntheses of Prelactone V and Prelactone B

The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from D-glucose. The synthesis involves isopropylidene acetal formation of D-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.

Total asymmetric syntheses of β-hydroxy-δ-lactones via umpolung with sulfur dioxide

Cyclic stereotriads and stereotetrads of the β-hydroxy-d-lactone type, e.g. prelactonesBandE, commonin polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy) penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-d-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The d-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3- dienes.

Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B

Catalytic and stoichiometric asymmetric sulfur ylide reactions were employed to prepare alkyl-aryl epoxide intermediates in a convergent manner. These epoxides were utilized in efficient syntheses of the mevinic acid analogue 1 and prelactone B. Graphical abstract.