175879-98-8

Basic information

• Product Name: 3-(benzyloxy)-1-(4-methoxyphenyl)-4-(3,6,6-trimethylbicyclo[3.1.0]hex-2-en-2-yl)-2-azetidinone
• Synonyms: 3-(benzyloxy)-1-(4-methoxyphenyl)-4-(3,6,6-trimethylbicyclo[3.1.0]hex-2-en-2-yl)-2-azetidinone
• CAS NO: 175879-98-8
• Molecular Formula: C26H29NO3
• Molecular Weight: 403.51336
• Mol File: 175879-98-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(benzyloxy)-1-(4-methoxyphenyl)-4-(3,6,6-trimethylbicyclo[3.1.0]hex-2-en-2-yl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(benzyloxy)-1-(4-methoxyphenyl)-4-(3,6,6-trimethylbicyclo[3.1.0]hex-2-en-2-yl)-2-azetidinone(175879-98-8)
• EPA Substance Registry System: 3-(benzyloxy)-1-(4-methoxyphenyl)-4-(3,6,6-trimethylbicyclo[3.1.0]hex-2-en-2-yl)-2-azetidinone(175879-98-8)

Safety Data

• Hazardous Substances Data: 175879-98-8(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 96393-72-5 (1R,5S)-(-)-3,6,6-trimethylbicyclo[3.1.0]hex-2-ene-2-carbaldehyde 
• 19810-31-2 Benzyloxyacetyl chloride 

Relevant articles and documents

Modulating steric effects in diastereoselective Staudinger reaction: Synthesis of optically pure cis-β-lactams

Diastereoselection in the synthesis of β-lactams (14 and 15) via ketene-imine cycloaddition (Staudinger reaction) using different chiral auxiliaries has been examined. While sterically demanding imines derived from bicyclic aldehyde (1) with a β chiral centre provided excellent selectivity, use of imines derived from bicyclic aldehyde (17) with a γ chiral centre was not effective. Improvement of stereoselectivity was also sought using imines (6 and 7) derived from chiral amines (2d,e) and chiral aldehyde (1). The bicyclic terpenoid skeleton of the chiral auxiliary in 1 was dismantled by ruthenium tetroxide oxidation to given multiply functionalized β-lactams-23a-d in good yield.