178860-79-2

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 72369-93-8 (2S,4R)-1-benzyloxy-2,4,5-trihydroxypentane 
• 4613-68-7 O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose 
• 3396-71-2 3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 114861-25-5 (3R,5S)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol 
• 116306-89-9 (3αR,5S,6αR)-5-(benzyloxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 100-51-6 benzyl alcohol 
• 188048-30-8 2-Benzyloxy-1-[(2R,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-ethanone 
• 188048-29-5 [(2S,3S)-3-(1-Benzyloxymethyl-vinyl)-oxiranylmethoxy]-tert-butyl-diphenyl-silane 
• 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 
• 188048-32-0 (R)-1-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-pentan-2-one 

Downstream Products

• 178860-73-6 ((2R,4R,6S)-6-Benzyloxymethyl-2-phenyl-[1,3]dioxan-4-ylmethoxy)-tert-butyl-diphenyl-silane 
• 188048-35-3 ((4R,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethoxy)-tert-butyl-diphenyl-silane 
• 178860-74-7 (2S,4R)-2,4-((S)-benzylidenedioxy)-1-benzyloxy-16-methylheptadec-5(E/Z)-ene 
• 178860-81-6 (2R,4S)-2,4-((R)-benzylidenedioxy)-5-benzyloxypentanal 
• 178860-80-5 (2R,4S)-2,4-((R)-benzylidenedioxy)-1-benzyloxy-5-hydroxypentane 

Relevant academic research and scientific papers

Revised structure and synthesis of flavolipin

The proposed structure of natural flavolipin was revised as N-[N-[(3R)- 15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl]-L-serine as a result of a synthetic study and biological activity tests, and its isomers synthesized in a stereocontrolled manner.

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.

Stereocontrolled synthesis of all stereoisomers of the proposed flavolipin

All four stereoisomers of flavolipin were synthesized from D-glucose in a stereocontrolled manner. None of them was identical with the reported natural product.