72369-68-7

Upstream product

• 191721-03-6 (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-ribofuranos-5-ylidene)amine N-oxide 
• 75-36-5 acetyl chloride 

Downstream Products

• 108182-64-5 (1S,2R)-1-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propane-1,2,3-triol 
• 108182-73-6 (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-enofuranose 

Relevant academic research and scientific papers

Higher glycosamino acid precursors: C7 and C8 aminodialdoses via regio- and stereoselective [3+2] cycloaddition of vinyl trimethylsilane to C-glycosyl nitrones

Protected C7 and C8 aminodialdoses were prepared stereoselectively from readily available C5 and C6 monosaccharide N-benzyl nitrones, by regio- and diastereoselective 1,3-dipolar cycloaddition reactions with vinyl trimethylsilane, followed by acetyl chloride-mediated cleavage of the 5-(trimethylsilyl)isoxazolidine formed. The cycloaddition reaction took place in moderate to good global yields (67-74%); estimation of diastereoselectivities from isolated yields showed total endo preference for the reaction of the D-galacto configured nitrone and high endo preference for the D-ribo analogue, but exo preference for the D-xylo configured substrate. Attack on the re face of the nitrone was predominant in all cases. The absolute configuration of one of the protected 3-(α-D-galacto-pentopyranos-5-yl)isoxazolidine products was assigned by X-ray crystallographic analysis, allowing correlation of the configuration at the new stereogenic centre in the corresponding aminodialdose. For non-crystalline isoxazolidines, configurations were assigned on the basis of NOESY experiments and/or chemical correlation. Combined yields of aminodialdoses coming from isoxazolidines having identical configuration at C(3) sometimes reached high values (up to 90%). These compounds are precursors of higher-chain glycosamino acids.