172293-72-0

Upstream product

• 141277-18-1 (3S,4S,5R)-tert-butyl <6-(p-bromobenzyloxy)-4,5-epoxy-3-hydroxy>hexanoate 
• 172691-23-5 (4S,5S)-5-[(S)-2-(4-Bromo-benzyloxy)-1-hydroxy-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one 
• 141277-17-0 (S)-3-[(2S,3S)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid tert-butyl ester 
• 172691-27-9 (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester 
• 172691-26-8 (S)-3-[(2R,3R)-3-(4-Bromo-benzyloxymethyl)-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid tert-butyl ester 
• 172691-22-4 (4S,5S)-5-[(S)-2-(4-Bromo-benzyloxy)-1-hydroxy-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one 

Downstream Products

• 1053643-71-2 (3S,4R,5S)-6-(4-Bromo-benzyloxy)-3,4,5-trihydroxy-hexanoic acid methoxy-methyl-amide 
• 172293-79-7 (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(1,3-dithia-2-cyclohexyl)-1-hexanone 
• 172293-74-2 (3S,4R,5S)-6-<(4-Bromobenzyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-N-methoxy-N-methylhexanamide 

Relevant academic research and scientific papers

Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a non-carbohydrate precursor was achieved in six steps (19percent yield) from a chiral, γ,δ-epoxy β-hydroxy ester, 3a, readily available from the corresponding α,β-epoxy aldehyde.The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

Synthesis of 2'-deoxynucleosides substituted in C-5'

Stereocontrolled lactonisation of γ,δ-epoxy β-hydroxyesters provides, after reduction, 2-deoxysugars in pyrano or furano form. After appropriate protection of the hydroxyl functions, these sugars can be converted to various 2'-deoxynucleosides with different configuration of the sugar moiety and an extra functionalisation at C-5.