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

• 637029-39-1 (4R,5R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-isopropyl-5-methyl-tetrahydro-pyran-2-one 
• 93215-51-1 1-tert-butoxy-1-(trimethylsiloxy)ethylene 
• 116660-67-4 (2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 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.

Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters

A versatile methodology for the asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters has been developed that relies on a series of Evans' aldol, hydroxyl-directed cyclopropanation, methanolysis, and Hg(II) mediated cyclopropane ring-opening reactions for stereocontrol.

A short and efficient synthesis of (+)-prelactone B

The asymmetric total synthesis of (+)-prelactone B, a biologically important natural β-hydroxy-δ-lactone derivative that contains a 2,3-trans-dialkylpyran ring system, is described. This approach involves the use of a very efficient oxazolidinone-mediated anti-aldol reaction, and a diastereoselective coupling between a ketene silyl acetal with an aldehyde followed by lactonization.