Deoxy mannojirimycin

The simple piperidine pelletierine from Punica granatum (pomegranate) (Punicaceae) and Duboisia myoporoides (Solanaceae) is an anthelmintic. The simple piperidine derivatives deoxy-mannojirimycin (DMJ) and deoxynojirimycin (DNJ) from Lonchocarpus species (Fabaceae) are glycosidase inhibitors because they are structurally similar to the pyranose (six-membered ring) sugar moieties of the glycosidase disaccharide substrates. 

Yokoyama et al. reported that the palladium-catalyzed cyclization of the carbamate 186 gave the piperidine 187, which was converted to 1-deoxy-mannojirimycin 188, with excellent diastereoselec-tivity (Scheme 62).133... 

Another paper describes the preparation of 1-deoxy-mannojirimycin (the C-2 epimer of (5)) either from D-mannose (with double inversion... 

Piperidine analogues of neuraminic acid are mentioned in Chapter 16, and a detailed n.m.r. study of N-methyl-l-deoxynojirimycin is referred to in chapter 21. 1-Deoxy-mannojirimycin is also mentioned in Chapter 19. 

Ding, Y, Hindsgaul, O, Syntheses of l-deoxy-3-5 -(l-thio-a-D-glucopyranosyl)-mannojirimycin and l-deoxy-3-0-(5-thio-a-D-glucopyranosyl)-mannojirimycin as potential inhibitors of endo-a-D-mannosidase, Bioorg. Med Chem. Lett., 8, 1215-1220, 1998. 

Dondoni, A, Merino, P, Perrone, D, Totally chemical synthesis of azasugars via thiazole intermediates. Stereodivergent routes to (—)-nojirimycin, (—)-mannojirimycin and their 3-deoxy derivatives from serine. Tetrahedron, 49, 2939-2956, 1993. 

D-Gulonolactone was similarly converted into 1-deoxy-L-mannojirimycin (57) and L-mannonolactam (58) in an overall yield 20 and 24%, respectively, from D-gulonolactone. 

Two groups have synthesized the E-ring moiety of calicheamicin as its methyl glycoside (60) or the A(-acetyl-derivative (62) from L-serine via serinal derivatives (59) and (61), respectively (Scheme 16). The same serinal derivative (61) was converted into the 4-amino-4-deoxy-L-ribose derivative (63) by an iterative one carbon chain-extension reaction sequence (Scheme 17), and into 3-deoxy-L-mannojirimycin and 3-deoxy-L-... 

The reaction of dihydroxyacetone phosphate (DHAP) with racemic or (R)-3-azido-2-hydroxypropanol under the influence of rhamnulose-1-phosphate aldolase or fuculose-1-phosphate aldolase afforded azidoketose intermediates which were converted by way of palladium-mediated reductive amination into a number of novel compounds including 1,6-dideoxy-D-galactojirimycin (24), 1,6-dideoxy-L-altojirimycin (25), 1-deoxy-D-talojirimycin (26), 1-deoxy-L-mannojirimycin (27) and 1-deoxy-L-rhamnojirimycin (28). ... 

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