167842-11-7

Basic information

• Product Name: (2S,4R,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptan-3-one
• Synonyms: (2S,4R,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptan-3-one
• CAS NO: 167842-11-7
• Molecular Weight: 378.627
• Mol File: 167842-11-7.mol

Chemical Properties

• CAS DataBase Reference: (2S,4R,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptan-3-one(167842-11-7)
• EPA Substance Registry System: (2S,4R,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptan-3-one(167842-11-7)

Safety Data

• Hazardous Substances Data: 167842-11-7(Hazardous Substances Data)

Upstream product

• 132489-33-9 (S)-2-benzyloxy-3-pentanone 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 164145-48-6 (2S,4R,5S)-2-benzyloxy-5-hydroxy-4,6-dimethyl-3-heptanone 

Downstream Products

• 332179-91-6 (4R,6R)-4-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxane 
• 332179-89-2 (E)-(3S,5S,7R,10S,11S)-1,11-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-10,12-dimethyl-tridec-8-ene-5,7-diol 
• 332179-79-0 (R)-4-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-(4-methoxy-benzyloxy)-butyraldehyde 

Relevant articles and documents

Remote 1,5-stereoinduction in boron aldol reactions of methyl ketones: Application to the convergent assembly of the 1,3-polyol sequence of (+)-roxaticin

By exploiting 1,5-anti stereoinduction in the boron aldol coupling of the β-alkoxy methyl ketones 6 and 8 with aldehydes 7 and 9, the convergent synthesis of 2, corresponding to the fully protected polyol sequence of the 30-membered macrolide, (+)-roxaticin (1), was achieved in an efficient manner (15 steps and 24.0% yield from ketone 15).

Manipulation of the aldol adducts from lactate-derived ketones. A versatile chiral auxiliary for the asymmetric synthesis of β-hydroxy carbonyl compounds

The ketones 1 and 2 can be transformed into a wide range of enantiomerically-pure anti and syn α-methyl-β-hydroxy ketones and aldehydes. The α'-methyl group in 5 and 11 may be retained, demonstrating the use of the lactate-derived group as an optional chi