188048-35-3

Upstream product

• 188048-30-8 2-Benzyloxy-1-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-ethanone 
• 100-51-6 benzyl alcohol 
• 188048-29-5 [(2S,3S)-3-(1-Benzyloxymethyl-vinyl)-oxiranylmethoxy]-tert-butyl-diphenyl-silane 
• 188048-32-0 (R)-1-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-pentan-2-one 
• 188048-28-4 (2S,3S)-(3-(1-(benzyloxy)prop-2-en-2-yl)oxiran-2-yl)methanol 
• 931407-65-7 4-(benzyloxymethyl)penta-2,4-dien-1-ol 
• 79629-41-7 (((2-bromoallyl)oxy)methyl)benzene 
• 77-76-9 2,2-dimethoxy-propane 
• 178860-79-2 (2R,4S)-1-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentane-2,4-diol 

Relevant academic research and scientific papers

Building Blocks for the Stereocontrolled Synthesis of 1,3-Diols of Various Configurations

A Sharpless epoxidation of the pentadienol 12 afforded the unsaturated epoxyalcohol 11 with 97.7% ee. Silylation of 11 and ozonolysis provided the epoxyketone 14. A completely anti-selective reduction of 14 succeeded with Zn(BH4)2. It led to the epoxyalcohol 15 which was converted into the acetonide alcohols 21 and 23, building blocks for enantiopure anti-1,3-diols. Alternatively, the same epoxyketone 14 and cp2Ti(III)Cl / 1,4-cyclohexadiene gave the β-hydroxyketone 16. This compound was transformed into the acetonide alcohols 22 and 24, building blocks for enantiopure syn-1,3-diols.