129279-37-4

Upstream product

• 14685-99-5 (-)-5-amino-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 501-53-1 benzyl chloroformate 
• 223142-14-1 (+)-(3aR,4'S,5R,5'S,6R,6aS)-3-(4',5'-diphenylimidazolid-2'-yl)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole 
• 223421-32-7 (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde 
• 85502-95-0 (+/-)-3-(diethoxymethyl)-3a,6a-dihydrofuro<2,3-d>isoxazole 
• 14685-99-5 (3aR,5R,6S,6aR)-5-((R)-1-Amino-2-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 

Downstream Products

• 223421-31-6 (+)-5-benzyloxycarbonylamino-5-deoxy-L-idofuranose 
• 383369-46-8 (1S,2R,3S,4R,5R)-N-(benzyloxycarbonyl)-2,3,4-trihydroxy-6-oxa-nor-tropane 

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

Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors

A practical synthesis of polyhydroxylated 6-oxa-nor-tropanes incorporating the essential structural features of calystegine B2 from 5-deoxy-5-thioureido and 5-ureido-L-idofuranose precursors is presented. The methodology relies on the ability of pseudoamide-type nitrogen atoms (thiourea, urea, and carbamate) to undergo nucleophilic addition to the masked aldehyde group of the monosaccharide. The generated hemiaminal functionality may further undergo in situ intramolecular glycosidation to give the bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect. A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver β-glucosidase was observed for 6-oxacalystegine B2 analogues incorporating aromatic pseudoaglyconic groups. On the basis of these data, a 1-azasugar inhibition mode is proposed for this family of glycomimetics.

Total syntheses of (+)- and (-)-1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D- and L-glucitol) and of (+)- and (-)-1-deoxyidonojirimycin (1,5-dideoxy-1,5-imino-D- and L-iditol) via furoisoxazoline-3-aldehydes

The isoxazoline obtained by 1,3-dipolar cycloaddition of 2,2-diethoxyacetonitrile N-oxide to furan was converted into enantiomerically pure (-)-(3aS,5S,6S,6aR)- and (+)-(3aR,5R,6R,6aS)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-carbaldehyde, (-)-5 and (+)-5, respectively, through resolution with (1S,2S)-1,2-diphenylethylenediamine. The aldehydes 5 are required as latent 1,5-iminohexitol moieties in cross-aldolizations towards imino-C-disaccharides. In order to establish absolute configurations of 5, and to probe the projected uses, (+)-5 was converted into (+)-1-deoxynojirimycin [(+)-1, 3 steps, 58%] and into (-)-1,5-dideoxy-1,5-imino-l-iditol [(-)-2, 4 steps, 40%] adopting stereoselective routes. Similarly, (-)-1,5-dideoxy-1,5-imino-l-glucitol ((-)-1) and (+)-1,5-dideoxy-1,5-imino-D-iditol ((+)-2) were obtained with the same ease. Copyright (C) 1998 Elsevier Science Ltd.