Nojirimycin analogues

R.-W. Wang, X.-L. Qiu, M. Bols, F. Ortega-Caballero, and F.-L. Qing, Synthesis and biological evaluation of glycosidase inhibitors gem-Difluoromethylenated nojirimycin analogues, J. Med. Chem., 49 (2006) 2989-2997. 

A. Dondoni, G. Fantin, M. Fogagnolo, and P. Merino, A divergent route to nojirimycin analogues from L-serinal and 2-acetylthiazole, J. Chem. Soc. Chem. Commun. p, 854 (1990). 

Fleet s group has reported syntheses of the nojirimycin analogues... 

Fig. 40 Synthesis of a-C-glycosyl derivative of nojirimycin and its analogues. Reagents and conditions (a) BnNH2, PTSA (b) CH2=CHCH2MgBr, Et20 (c) FmocCl, Na2C03 (d) PCC (e) piperidine, DMF (f) NaHB(OAc)3, AcOH, Na2S04, 1,2-dichloroethane, -35 °C.

A. Amone, P. Bravo, A. Donadelli, and G. Resnati, Fluorinated analogues of nojirimycin and mannojirimycin from a non-carbohydrate precursor, Tetrahedron, 52 (1996) 131-142. 

Amidine and Guanidine Derivatives - The A/-alkyl-D- ucosamidinium salts 63 have been synthesized by condensation of nojirimycin with the appropriate amine followed by oxidation with iodine. Amidine-linked pseudo-disaccharide 66 has been synthesized by reaction of the thionolactam 64 with the 6-amino-sugar 65 (Scheme 16), and a (l- 4)-linked analogue has been obtained similarly. ... 

A paper on the use of 1,6-anhydro-hexoses for oligosaccharide synthesis includes a conversion of 1,6-anhydro-2,3-di-0-benzyl-(5-D-glucofuranose to the corresponding 5-azido-5-deoxy analogue (17) by a double inversion sequence, and hence to 1-deoxy-nojirimycin (18)/... 

Vogel has applied his naked sugar chemistry to the synthesis of 5-C-methyl-nifo-nojirimycin (60), and its 6-deoxy-analogue, from the bicyclic lactone (58) derived from a chiral 7-oxanorbomane (Scheme 17). The amino-group was introduced by Curtius rearrangement of the acyl azide (59). ... 

Borohydride reduction of 2-amino-2-deoxy-D-manno- and -D-gluco-furanurono-3>6-lactones gave the 1-deoxynoJirimycin analogues (63) and (64) respectively in good yield.The dissociation of the nojirimycin-bisulphite adduct has been examined and the cyclic structure (65) suggested. The anomeric effect in nojirimycin is referred to in Chapter 20. 

From Aminoacids. - Syntheses of aminosugars from serine and threonine have been reviewed. Dondoni and co-workers used their thiazole chain extension methodology to prepare L-nojirimycin 46 and L-mannonojirimycin 47 from the L-serine derived aldehyde 44 (Scheme 12). As well, they reported alternative routes to 45,46 and 47 and an improved synthesis of the protected methyl glycosides of the 3-deoxy-analogues of 46 and 47 (cf. Vol.24, p.llS), all from 44. They have also devel( )ed an improved method to convert various carbohydrate thiazole derivatives to the corresponding aldehydes (with i,MeOTf ii,NaBH4 and iii,Cu<32 CuO) in yields of 70-85%. The... 

Godin G, Compain P, Masson Gr, Martin OR. A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate. J. Org. Chem. 2002 67 6960-6970. 

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