99249-33-9

Basic information

• Product Name: (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.6]undec-7-ene
• Synonyms: (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.6]undec-7-ene
• CAS NO: 99249-33-9
• Molecular Weight: 394.511
• Mol File: 99249-33-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.6]undec-7-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.6]undec-7-ene(99249-33-9)
• EPA Substance Registry System: (2S,3S)-2,3-Bis-benzyloxymethyl-1,4-dioxa-spiro[4.6]undec-7-ene(99249-33-9)

Safety Data

• Hazardous Substances Data: 99249-33-9(Hazardous Substances Data)

Upstream product

• 1121-66-0 2-Cyclohepten-1-one 
• 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.