1.4- dideoxy-1,4-imino- -D-arabinitol

When 2-azidoaldehydes are used as substrates in the RAMA-catalyzed aldol reaction with dihydroxy acetone phosphate (DHAP), the azidoketones thus obtained can be reduced into the corresponding primary amines. Subsequent equilibration to imine intermediates, followed by reduction, generates the corresponding pyrrolidines (Scheme 13.16) [22,33]. 1,4-Dideoxy-1,4-imino-D-arabinitol 11 was prepared from azidoacetaldehyde. Both 2R,5R) and 2S,5R)-bis(hydroxymethyl)-(3R,4R)-dihydroxypyrrolidine (12 and 13) were derived from racemic 2-azido-3-hydroxypropanol. The aldol product resulting from kinetic control was converted into the (2R,2R) derivative 12, whereas the product resulting from thermodynamic control gave the... 

Dideoxy-1,4-imino-D-arabinitol (D-AB1) (7) Angylocalyx spp. (Leguminosae) seeds/leaves/bark [6] Arachniodes standishii (Polypodiaceae) leaves [7] Eugenia spp. (Myrtaceae) leaves/bark [8] Hyacinthoides non-scripta (Hyacinthaceae) bulb/leaves [8] Moms bombycis (Moraceae) leaves [9]... 

Dideoxy-1,4-imino-D-arabinitol (D-AB1) potent inhibitor of a-glucosidase [64,65] and a-D-arabmosidase [66]... 

Jamali, B., and Nielsen, H. M. (2003). Development and validation of a capillary electrophoresis-indirect photometric detection method for the determination of the non-UV-absorbing 1,4-dideoxy-l,4-imino-d-arabinitol in active pharmaceutical ingredients, solutions and tablets using an internal standard. J. Chromatogr. A 996(1—2), 213-223. 

Compounds (9) and (10) have also been synthesized by an enzyme-catalysed process as indicated in Scheme 5 1,4-dideoxy-l,4-imino-D-arabinitol was also made from the same azido-hydroxypropanal using... 

A combined enzymatic/chemical synthesis of imino-alditols used fructose 1,6-diphosphate aldolase to generate 6-azido-ketohexoses (as outlined in Scheme 4) which could be catalytically reduced to deoxynojirimycin and deoxymannojirimycin. By use of appropriate azido-aldehydes, fagomine(15) and 1,4-dideoxy-l,4-imino-D-arabinitol (16) were similarly prepared. Microbial epimerization of 1-deoxy-... 

Dideoxy-1,4-imino-(2-0-P-D-ElucopyranosvD-D-arabinitol weak inhibitor of a- and P-glucosidases ... 

In enantiospecific syntheses, (+)- (34) and (—)-l-azafagomine have been prepared from 2,3,5-tri-O-benzyl-D- and -L-xylose respectively e.g. as depicted in Scheme 9 for the D-xylose). As a consequence of these syntheses, the glucosidase activity of ( + )-l-azafagomine was found to be entirely due to the (—)-enan-tiomer. A more direct route to 34, requiring a double displacement of the mesylate groups in 33 with hydrazine, was attempted. However, iV-amino-1,4-dideoxy-l,4-imino-L-arabinitol 35 was the only product isolated. ... 

Several papers have dealt with pyrrolidine analogues. D-Xylose has been converted routinely to 4-amino-4-deoxy-L-arabinose, which on hydrogenation in weakly acid solution yielded 1,4-dideoxy-l,4-imino-L-arabinitol.Full details of a synthesis of 2,5-dideoxv-... 

AT-Methyl- and -butyl-derivatives of deoxynojirimycin, l,4-dideoxy-l,4-imino-D-arabinitol and 2,S-dideoxy-2,5-imino-D-mannitol have been studied by NMR spectroscopy to provide data for determining a conformational basis for the inhibition of glycosidase and HIV-1 replication activity by these types of compounds. ... 

The use of (S)-pyroglutamic acid as a non-carbohydrate starting material for the preparation of l,4-dideoxy-l,4-imino-D-arabinitol 41 has been reported, whilst a synthesis of l,4-dideoxy-l,4-imino-L-arabinitol from the D-lyxono-1,4-lactone 42, in which the key steps involve inversions at C-2 and C-4 by sulfonate displacement reactions, has also been described. ... 

C.H. Von Der Osten, A.J. Sinskey, C.E Barbas III, R.L. Pederson, Y.F Wang, C.-H. Wong, Use of a recombinant bacterial fructose-1,6-diphosphate aldolase in aldol reactions preparative syntheses of 1-deoxynojirimycin, 1-deoxymannojirimycin, l,4-dideoxy-l,4-imino-D-arabinitol, andfagomine, I. Am. Chem. Soc. Ill (1989) 3924-3927. 

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