1-Deoxynojirimycin glucopyranosides

The L-fuco analogue of 1-deoxynojirimycin, l,5-dideoxy-l,5-imino-L-fucitol or 1-deoxy-L-fuconojirimycin (51), was first synthesized by Fleet and co-workers in 1985 by a multi-step sequence starting from methyl-a-o-glucopyranoside... 

Aminomercuration aminoalditols The synthesis of the natural aza-alditol 1-deoxynojirimycin (4) from methyl a-D-glucopyranoside involves the reductive ring-opening (Zn) and reductive amination (NaBH3CN) of 1 to give 2 in 91% yield. Aminomercuration of 2 results mainly in the bromomercurial 3, which was converted into the aza-sugar 4 by reductive oxygenation and deprotection. 

Deoxynojirimycin-2-O-, 3-0-, 4-0- a-D-ghicopyranosides and 2- 0-, 6-O-a-D-galactopyranosides and 2-0, 4-0-, 6-0-(3-D-glucopyranosides Morns alba (Moraceae) roots [ 10] Streptomyces lavandulae GC-148 [24]... 

Methyl (3-D-glucopyranoside (6) has been used for the synthesis of 1-deoxynojirimycin... 

Deoxymannojirimycin has been synthesized with excellent diastereoselec-tivity in a process based upon a palladium(II)-catalysed cyclization of an allylic alcohol 62 derived from D-mannitol. C-6 Homologues of 1-deoxynojirimycin and 1-deoxy-L-idonojirimycin (l,5,6-trideoxy-l,5-imino-D-gf/Mco- and -h-ido-heptitols) have also been prepared using palladium chemistry. In these reports the protected aminohex-l-enitol 63, derived from methyl a-D-glucopyranoside, was amino-carbonylated in the presence of palladium(II) chloride to afford a mixture of cyclized products whose composition was dependent upon the reaction conditions utilized. Two of these products, 64 and 65, were reductively transformed into the DNJ and 1-deoxy-L-idonojirimydn homolgues respectively 58,59... 

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