20187-74-0

Upstream product

• 100-39-0 benzyl bromide 
• 4860-82-6 2,3-anhydro-α-D-ribofuranoside de methyle 
• 168554-40-3 methyl 5-O-benzyl-2-deoxy-2-fluoro-α-D-lyxofuranoside 
• 173676-14-7 Toluene-4-sulfonic acid (2R,3S,4S,5S)-2-benzyloxymethyl-4-fluoro-5-methoxy-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Fluoroglycolactone synthesis method

The invention discloses a synthesis method of fluoro sugar lactone. According to the method, D-xylose is taken as a starting raw material, hydroxyl is protected to synthesize a lactonide compound intermediate, and then the fluoroglycolactone is obtained through the steps of stereo conversion of sugar cyclic alcohol, benzyl addition, methyl glycoside removal, hydroxyl oxidation and the like. The raw materials adopted by the synthesis method are simple, cheap and easy to obtain, each synthesis step is mild in condition, the treatment process is simple, the yield is relatively high, and new raw materials and synthesis ways are provided for design of fluorine-containing bioactive molecules.

Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides

The oxidation of methyl 5-O-benzyl-3(2)-deoxy-3(2)-fluoro-α-D-pentofuranosides with dimethyl sulfoxide-acetic (trifluoroacetic) anhydride was accompanied by epimerization at the carbon atom bearing a fluoro function, resulting in the formation of the corresponding 2- or 3-keto derivatives as mixtures of two epimers in high combined yield.Reduction of a mixture of the erythro/threo epimeric 2-keto sugars (isolated as stable hydrates) with sodium borohydride in benzene-ethanol proceeded stereoselectively leading to the formation of 3-deoxy-3-fluoro ribo- and lyxo-furanosides, respectively.In the case of the ribo and arabino epimers of the 3-keto sugar (isolated as free ketones), reduction stereoselectivity of the former was >95percent for the 2-deoxy-2-fluoro ribo sugar, whereas a ca. 3:1 lyxo/arabino ratio of products was obtained for the latter.Treatment of a mixture of the 2-epimeric 3-keto sugars with triethylamine in carbon tetrachloride at room temperature for 3-5 h afforded the 2-deoxy-2-fluoro ribo ketone (ca. 90percent).The synthesis of 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-lyxofuranose (8) and 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoeo-β-D-ribofuranose (16) and their use as glycosylating agents for bis-trimethylsilylated N6-benzoyladenine is described.Keywords: Fluorodeoxy pentafuranosides; Keto sugars; Epimerization