110677-94-6

Basic information

• Product Name: 3-<(1-methyl)ethylidine>cyclopentan-1-one 1,4-di-O-benzyl-L-threitol
• Synonyms: 3-<(1-methyl)ethylidine>cyclopentan-1-one 1,4-di-O-benzyl-L-threitol
• CAS NO: 110677-94-6
• Molecular Weight: 408.538
• Mol File: 110677-94-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-<(1-methyl)ethylidine>cyclopentan-1-one 1,4-di-O-benzyl-L-threitol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-<(1-methyl)ethylidine>cyclopentan-1-one 1,4-di-O-benzyl-L-threitol(110677-94-6)
• EPA Substance Registry System: 3-<(1-methyl)ethylidine>cyclopentan-1-one 1,4-di-O-benzyl-L-threitol(110677-94-6)

Safety Data

• Hazardous Substances Data: 110677-94-6(Hazardous Substances Data)

Upstream product

• 1619-28-9 3-isopropyl-cyclopent-2-enone 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 

Relevant articles and documents

HOMOCHIRAL KETALS IN ORGANIC SYNTHESIS. DIASTEREOSELECTIVE CYCLOPROPANATION OF α,β-UNSATURATED KETALS DERIVED FROM 1,4-Di-O-BENZYL-L-THREITOL

2-Cykloalken-1-one 1,4-di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent.For example, 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal gave in 90-98percent yield a 9:1 mixture of diastereomeric cyclopropanes as established by 62.9 MHz 13C NMR spectroscopy and by hydrolysis of the mixture to (1R,6S)-bicycloheptan-2-one.Sixteen other examples are presented which demonstrate the generality and predictability of the process for 2-cycloalken-1-one ketals, as well as an unfortunate lack of diastereoselectivity for α,β-unsaturated 1,4-di-O-benzyl-L-threitol acetals.