133006-37-8

Basic information

• Product Name: (-)-(3S,5S,6S)-8-(benzyloxy)-6-hydroxy-2,2,5-trimethyl-3-<(trimethylsilyl)oxy>-4-octanone
• CAS NO: 133006-37-8
• Molecular Weight: 380.6
• Mol File: 133006-37-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-(3S,5S,6S)-8-(benzyloxy)-6-hydroxy-2,2,5-trimethyl-3-<(trimethylsilyl)oxy>-4-octanone(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(3S,5S,6S)-8-(benzyloxy)-6-hydroxy-2,2,5-trimethyl-3-<(trimethylsilyl)oxy>-4-octanone(133006-37-8)
• EPA Substance Registry System: (-)-(3S,5S,6S)-8-(benzyloxy)-6-hydroxy-2,2,5-trimethyl-3-<(trimethylsilyl)oxy>-4-octanone(133006-37-8)

Safety Data

• Hazardous Substances Data: 133006-37-8(Hazardous Substances Data)

Upstream product

• 19790-60-4 3-Benzyloxypropanal 
• 133006-32-3 (S)-(-)-5,5-dimethyl-4-<(trimethylsilyl)oxy>-3-hexanone 
• 133006-33-4 (S)-5,5-Dimethyl-4-triisopropylsilanyloxy-hexan-3-one 
• 21641-92-9 (S)-2-hydroxy-3,3-dimethylbutanoic acid 
• 133006-31-2 (S)-(+)-4-hydroxy-5,5-dimethyl-3-hexanone 
• 20859-02-3 L-tert-Leucine 

Relevant articles and documents

Protocols for the Preparation of Each of the Four Possible Stereoisomeric α-Alkyl-β-hydroxy Carboxylic Acids from a Single Chiral Aldol Reagent

Protocols have been devised whereby all four possible stereoisomeric α-alkyl-β-hydroxy carboxylic acids can be derived from a single aldol reagent, hydroxy ketone 3.Compound 3, obtained in enantiomerically homogeneous form in 50percent overall yield from tert-butylglycine (1), is used for aldol reactions in the form of its trimethylsilyl and tert-butyldimethylsilyl derivatives, 4 and 5.The Z lithium and Z boron enolates of 4 react with various aldehydes to give aldols 8 and 9, respectively.Deprotonation of 4 by bromomagnesium 2,2,6,6-tetramethylpiperidide (MTMP) gives the E enolate, which may be trapped by trimethylsilyl chloride to obtain the E silyl enol ether 11.The E bromomagnesium enolate of 4 reacts with aldehydes to give aldols of structure 15.Transmetalation of the bromomagnesium enolate of keto ether 5 is accomplished by reaction with (triisopropoxy)titanium chloride.The resulting E (triisopropoxy)titanium enolate reacts with aldehydes to provide aldols of structure 17.The aldols resulting from the foregoing reactions are hydrolyzed to keto diols 19-22, which are oxidized to the stereoisomeric α-methyl-β-hydroxy carboxylic acids 23-26.