Amino-alditols

C-5 being determined by reduction of the intermediate imine from its 

Dimethyl galactarate serves as a source of 1,6-diamino-l,6-di-deoxy-galactitol, using a di-amide derivative to introduce the 

1-amino-1-deoxy-D-mannitol derivatives. Surface-active 2-acyl- 

6-Amino-l,5-anhydro-6-deoxy-D-glucitol, prepared in standard reactions from D-glucose, has been used to prepare compounds (26) 

The oxiran-aldonates (27) undergo intramolecular rearrangement via orthoester intermediates to give 2,5-anhydro-aldonates, which were used to make DL-epiallomuscarine (28) and DL-epimuscarine (29) 

---

L. E. Fellows, E. A. Bell, D. G. Lynn, F. Pilkiwicz, I. Miura, and K. Nakanishi, Isolation and structure of an unusual cyclic amino alditol from a legume, J. Chem. Soc., Chem. Commun. (1979) 977-978. 

Alditols and Amino-alditols. - A preparation of the tetritol (Cs-Ce) fragment, 1, of the macrolactone (+)-aspicilin, featured the desymmetrization of meso-erythritol through the formation and subsequent base-promoted dia-stereoselective acetal fission of a C2-symmetric his-sulfoxide intemediate, (Scheme 1,2- 3). ... 

Isomeric glucosylated amino-alditol derivatives, 17, derived from reaction of 2-amino-2-deoxy-mannit-6-yl and -glucit-6-yl a-D-glucopyranosides with methyl methacrylate, were co-polymerized and the physical properties of the resulting polymers were examined in water. 

Cyclic imino derivatives of amino-alditols.- Several laboratories have reported studies on these compounds, which can show glycosid-ase inhibitory activity. Fleet s group has studied the plant alkaloids (22)-(24) which are analogues of glucose, fructose, and mannose respectively analysis of the inhibitory activity of these compounds towards a variety of glycosidases has shown that the... 

Reductive amination reaction of the reducing carbohydrate with primary aromatic or heterocyclic amines in the presence of sodium cyano-borohydride yielding the corresponding amino-alditols, e.g.. 

Amino alditols, derived from nitro alditols and from glycosylamines (Chapter VIII), may be converted to polyols by treatment with nitrous acid, but anhydro rings may be formed (p. 378). 

Alditols Acyclic Alditols Anhydro-Alditols Amino-Alditols... 

Syntheses of amino-alditol derivatives are covered in Chapters 18 and 19, and the introduction of a 2-acetamido-function into a sugar formazan derivative is covered in Chapter 10. 

Amino-Alditols. - Aldose oximes, e.p... of mannose and arabinose, can be reduced electrochemically to 1-aminoalditols glucose oxime reacted differently, because, it is proposed, of its strong tendency to cyclize to an N-glucosyl hydroxylamine derivative. l-Amino-2-acetamido-1,2-dideoxy-D-alditols have been prepared by sodium cyano-borohydride reduction of 2-acetamido-2-deoxy-glycosylamines (D-Glc, D-Man, and D- lc-D-Glc).6-(5-deoxy-D-ribit-5-yl)amino-uracil has been condensed with 2-chloro-4-hydroxybenzaldehyde to give a flavin derivative which was further elaborated to Redox Coenzyme Factor 420. ... 

Amino-Alditols. - Diaminodideoxytetritols have been prepared by standard procedures from butene-diol, mannitol, and tartaronitrile precursors to give stereoisomers of 1,4- or 2,3-diamino compounds... 

Oligosaccharide 1-deoxy-l-(4-trifluoroacetamidophenyl)amino-alditols can be oxidized to the corresponding reducing oligosaccharides with hydrogen peroxide, or to the corresponding 1-amino-l-... 

The synthesis of amino-alditol derivatives of naturally occurring hydrolysable tannins is mentioned in Chapter 7 and the preparation of some C-6 and C-7 analogues of lV-acetyl-6-amino-2,6-dideoxyneuraminic acid as well as the isolation and synthesis of the fungal metabolite nectrisine are covered in Chapter 9. The synthesis of 4-0-(p-D-galactopyranosyl) derivatives of deoxynojirimycin can be found in Chapter 3 and castanospermine derivatives are covered in Chapter 24. 

Amino-Alditols.- Anti-selective reduction of acyclic or-alkoxy and of, -dialkoxy ketone oximes occurs with aluminium hydride reagents, L-threo-ketotetrose derivatives (24) giving L-xylitol... 

A sensitive method for analysis of the constituent monosaccharide components of glycoproteins involved sequential acid hydrolysis, borotrltide reduction, re-N-acetylation, and radioactivity detection after separation of neutral alditols and amino-alditols on a cation-exchange resin in the Pb -form at 80°C. ... 

Maugard, T., Remaud-Simeon, M. and Monsan, P. (1998) Kinetic study of chemoselective acylation of amino-alditol by immobilized lipase in organic solvent effect of substrate ionization. 

---