300578-08-9

Basic information

• Product Name: (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one
• Synonyms: (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one
• CAS NO: 300578-08-9
• Molecular Weight: 369.319
• Mol File: 300578-08-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one(300578-08-9)
• EPA Substance Registry System: (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one(300578-08-9)

Safety Data

• Hazardous Substances Data: 300578-08-9(Hazardous Substances Data)

Upstream product

• 1666-13-3 diphenyl diselenide 
• 34837-55-3 Phenylselenyl bromide 
• 79-50-5 (S)-pantolactone 

Relevant articles and documents

Intermolecular and intramolecular reactions of resolved 2-alkoxytetrahydrofuran-3-yl and 2-alkoxytetrahydropyran-3-yl radicals

Diastereomeric trans-2-alkoxy-3-phenylselenenyltetrahydrofuranyl acetals and trans-2-alkoxy-3-phenyl-selenenyltetrahydropyranyl acetals were prepared from dihydrofuran, dihydropyran, phenylselenenyl bromide, and the alcohols (S)-methyl lactate, (S)-methyl hexahydromandelate, and (R)-pantolactone. The diastereomers were chromatographically separated and were subjected to intermolecular alkylation via generation and trapping of free radicals. Observed diastereoselectivity was higher for 2-alkoxytetrahydrofuran-3-yl radicals than for 2-alkoxytetrahydropyran-3-yl radicals, and highest for acetals involving (R)-pantolactone. Alcohol exchanges at the anomeric carbon were highly stereocontrolled, and permitted introduction of alkenes for intramolecular trapping of free radical intermediates. (C) 2000 Elsevier Science Ltd.