1401337-53-8

Basic information

• Product Name: (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate
• CAS NO: 1401337-53-8
• Molecular Weight: 432.676
• Mol File: 1401337-53-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate(1401337-53-8)
• EPA Substance Registry System: (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate(1401337-53-8)

Safety Data

• Hazardous Substances Data: 1401337-53-8(Hazardous Substances Data)

Upstream product

• 133467-37-5 (4S)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-benzyl-2-oxazolidinone 
• 100-52-7 benzaldehyde 
• 149400-42-0 ethyl (2E,4E)-4-methylhexa-2,4-dienoate 
• 220173-96-6 (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-3-phenylpropan-1-ol 
• 220173-95-5 (S)-7-benzyl-3-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-3-phenylpropanoyl]oxazolidin-2-one 

Relevant articles and documents

Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products. The Royal Society of Chemistry 2012.