3- Amino-3-deoxy-D-mannose

In the case of 3-amino-3-deoxy-D-mannose. a detailed analysis of the reaction indicated that the dithioacetal is fotmed tmder kinetic control, followed by equilibration to afford a mixture of products, the relative amounts of which are dependent an their thermodynamic stabilities [32]. 

The alkaloid has been synthesised from two starting materials (a) from methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-a-D-mannopyranoside (t. Suami, K. Tadano and Y. limura, Carbohydr, Res., 1985, 136, 67) and (b) from 3-amino-3-deoxy-D-mannose (M.H. Ali, L. Hough and R.C. Richardson, ibid., p.225). 

L-arabinose. A paper-chromatographic study of the mercaptalation reaction with n-galactose, D-glucose, and D-mannose confirmed that almost complete conversion to the dithioacetal occurred within 5 minutes, but, after several hours, an equilibrium was set up in which two 1-thio-glycosides, probably the anomeric pyranosides, the dithioacetal, and the free aldose were all present the 1-thioglycoside was particularly favored with the D-mannose structure. 3-Amino-3-deoxy-D-mannose reacted (qualitatively) similarly to D-mannose, but more slowly, probably because of the polar influence of the amino group. 

Glycosyl Halide Derivatives of 3-Amino-3-deoxy-D-mannose, M. L. Wolfrom, H. G. Garg, and D. Horton,/. Org. Chem., 28, 2989-2992 (1963). 

D-glucose as the chiral starting material, the former being converted to a 4-amino-4-deoxy-D-mannose intermediate, the latter to a 3-amino-3-deoxy-D-mannose derivative. The adenosine deaminase inhibitor (+)-EHNA (60) has been prepared using L-ascorbic acid as the source of the chiral oxiran precursor (61). 

In this manner 3-amino-3-deoxy-D- and -L-ribose, 3-amino-3-deoxy-D-mannose and 3-amino-3-deoxy-D-glucose have been prepared. In an analogous way Richardson and Fischer , starting from laevoglucosan, obtained 3-amino-i,6-anhydro-3-deoxy-D-glucose, -D-altrose and -D-idose. 

As 2-amino-2-deoxy-D-mannose is tumorstatic and 2-acetamido-2-deoxy-D-mannose 6-phosphate is an obligatory intermediate in the biosynthetic pathway to sialic acid, displacement of the essential OH-6 with a fluorine atom should be interesting from the biological viewpoint. 2-Acetamido-1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-D-mannopyranose (see Table 111 in Section 11,3) and its O- and A,0-deacetyl derivatives were prepared the first compound showed weak anticancer activity. 

Trisaccharides with 2-amino-2-deoxy-D-mannose and -galactose termini to have been synthesized are g-a-D-Glcg -Cl 3) g-a-L-Rha ( 1 -> 3)-3-D-ManNAc (the repeating unit of the 0-speciflc... 

D-Mannosamine 2-amino-2-deoxy-D-mannose, an amino sugar related to mannose (the hydroxyl group on C2 of mannose is replaced by an amino group). M, 179.17, m.p. of the hydrochloride 180°C, [a]o -3°. M. is a constituent of neuraminic acids, animal mucolipids and animal mucoproteins. 

Halogen-. Nitrogen-. Sulphur- and Seleno-containinq Compounds.-1,3,4,6-Tetra-Q-acetyl-2-deoxy-2-fluoro-/8-D-galactopyranose,the tricyclic fluoride (11), 4,1, 6 -trichloro-4,l, 6 -trideoxy-galacto-sucrose.the iodo-aldulose derivative (12), 6-deoxy-6-iodo-l,2 3,4-di-Q-isopropylidene-a-D-galactopyranose,allyl 1-deoxy-l-[(l-methyl-2-benzoyIviny1)amino)-a-D-fructofuranoside, the 1,6-lactam (13), the natSiral products alexine (14) and 3,8-diepialexine (15), the 2-amino-2-deoxy-D-mannose derivative... 

The lipopolysaccharide of Chromatium vinosum contains 3-G-methyl-D-ribose, D-ribose, L-arabinose, D-glucose, and 2-amino-2-deoxy-D-mannose, and smaller proportions of D-rhamnose, 3-deoxy-2-octulosonic acid, and 2-amino-2,6-dideoxy-D-glucose (quinovosamine). D-glycero-D-manno-HQptose but not L-glycero-B-manno-heptose, was also tentatively identified. The composition of the lipopolysaccharide from Coxiella burned has been reported. ... 

Studies have revealed that the deamination of 2-amino-2-deoxy-D-glucosides is more complicated than previously supposed. It has been reported that methyl 2-amino-2-deoxy-a- and -/3-d-glucopyranoside give, in addition to 2,5-anhydro-D-mannose, methyl 2-deoxy-2-C-formyl-a- and -/S-D-ribofuranoside (for example, 97 to 98) in yields of 25 and 19%, respectively, under the experi-... 

SUBSTITUTED PYRAZINE 1-OXIDES FROM 2-AMINO-2-DEOXY-D-GLUCOSE (OR MANNOSE) OXIME WITH GLYOXAL... 

D- rafro-Tetrahydroxybutyl)pyrazine 1-oxide (7) has been prepared by Fujii and Kobatake (543, 544) by the condensation of 2-amino-2-deoxy-D-glucose oxime (6) or 2-amino-2-deoxy-D-mannose oxime with glyoxal in water at room temperature. 

Preparations of pyrazine A -oxides containing extranuclear hydroxyl groups are also described in Qiapter III as follows Section III.l, 2-aminopyrazine 1-oxides from a-amino nitriles and a-hydroxyimino carbonyl compounds (540, 541) Section III.2, 3-substituted pyrazine 1-oxides from 2-amino-2-deoxy-D-glucose(or mannose) oxime with glyoxal (543, 544) and Section III.5, ring closure of the C-C-N-C-C-N-0 system (553). 

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