195519-71-2

Upstream product

• 72277-35-1 (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 108788-49-4 ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 

Downstream Products

• 108788-46-1 3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose 
• 108788-47-2 3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-α-D-glycero-L-ido-hepto-1,4-furanose 

Relevant academic research and scientific papers

Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

The Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol 4 afforded α- and β-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction cond

114. Aza-claisen rearrangement: Synthesis of 5'-branched 5'- aminothymidines

The syntheses of both diastereoisomers of 5'-ethyl-substituted thymidine dimers, the (5'R)- and (5'S)-configurated 33a and 33b, respectively, in which the natural phosphodiester linkage is replaced by an amide group (C(3')- CH2CONH-CH(5')(Et)), are described. Their fully protected derivatives 35a and 35b, respectively, are suitable for incorporation into antisense oligonucleotides. Unexpectedly, an attempted Pd(II)-catalysed aza-Claisen rearrangement of trichloroacetimidate 7 provided the diastereoisomerically pure cyclopropane derivative 17, whose structure was confirmed by X-ray analysis.