Pseudo-disaccharides synthesis

Pearce, A J, Sollogoub, M, Mallet, J M, Sinay, P, Direct synthesis of pseudo-disaccharides by rearrangement of unsaturated disaccharides, Eur. J. Org. Chem., 9, 2103-2117, 1999. 

Pelyvas, I. F., Madi-Puskas, M., Toth, Z. G., Varga, Z., Hornyak, M., Batta, G., Szlaricskai, F. Synthesis of new pseudo-disaccharide amino glycoside antibiotics from carbohydrates. J. Antibiot. 1995, 48, 683-695. 

S. Ogawa and H. Sugizaki, Synthesis of a pseudo-disaccharide derivative having d-manno configuration, an acarviosin analog, Chem. Lett., 17 (1986) 1977-1980. 

DOrner and Westermann [149] reported the preparation of the pseudodisaccharide 143 with a triazole tether (Scheme 37) as a prototype for the synthesis of carbohydrate-containing macrocycles, through a Huisgen-catalysed reaction and ring-closing methathesis as the key steps. Standard conditions were used, Cu(OAc)2 and sodium ascorbate as the Cu(I) source and a mixture of water and f-BuOH as solvent, for the conversion of protected glucopyra-nosyl azide 141 into pseudo-disaccharide 143 by using dialkyne 142 in a 77% yield. 

Anhydromaltose has been converted to the pseudo-disaccharides (25) containing 3-amino-3-deoxy-epz-inositol or 1-amino-l-deoxy-l-L-myo-inositol via the 6-deoxy-6-nitromaltose derivative (26). The branched-chain unsaturated 6-nitro-sugar (27), prepared conventionally from D-glucose, yielded isomeric dithianyl adducts which were similarly cyclized to give the nitro-cyclitols (28) and (29), of interest as potential intermediates for the synthesis of tetrodo-... 

Paulsen s group has transformed the protected streptosyl chloride (or bromide) (521 RS = Ph,H) into dihydrostreptosylstreptidine (522) and related pseudo-disaccharides. ° ° The 2,3-0-benzylidene derivatives (521 R R = Ph,H) yielded a-linked glycosides of L-streptose preferentially, whereas the 2,3-carbonates (521 R R = O) gave / -linked glycosides e.g. with cyclohexanol and l,2,3,4-tetra-0-acetyl-)5-D-glucopyranose). ° This work culminated in the synthesis of D-streptobiosamine (523) and its L-enantiomer (a disaccharide unit of streptomycin) by a route that involved condensation of methyl a-o(or L)-strepto-side 3 -(trimethylene dithioacetal) with the nitrosyl chloride adduct of 3,4,6-tri-O-acetyl-D-(or L)-glucal. ... 

Reviews have appeared on the synthesis of aminoglycoside antibiotics, and on the formation of new aminocyclitol antibiotics by mutants of amino-cyclitol-producing organisms fed with aminocyclohexanol or related subunits. The structures of eight minor components of the nebramycin complex elaborated by Streptomyces tenebrarius have been elucidated besides neamine and related pseudo-disaccharides, the new components are pseudo-trisaccharides related to kanamycin B, and the 3 -hydroxy analogue of the principal component of the complex, apramycin (see Vol. 10, p. 130). ... 

The synthesis of pseudo-disaccharides such as laminarabinose (78) by coupling the known Carbohydr. Res., 1985,136, 77) 5a-carba-l,2 4,6-di-0-isopropylidene laminarabinose-a or p-D,L-gIucopyranose with 2,3,4,6-tetra-O-acetyl-a-D-... 

C.-F. Valenza, S. Picasso, A. Goti, and A. Brandi, Straight-forward synthesis of (l->-2)-linked pseudo and aza-C-disaccharides by the novel cycloaddition of enantiopure cyclic nitrones to glycals, J. Org. Chem., 63 (1998) 7311-7318. 

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