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1772-03-8

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Synthesis of N-protected galactosamine building blocks from D-tagatose via the heyns rearrangement
N-Acetyl-D-galactosamine (11), a very important naturally occurring building block of oligosaccharides, is easily accessible via the Heyns rearrangement of D-tagatose (3) with benzylamine. The short and efficient synthesis of various differently N-protected D-galactosamine derivatives is reported. Copyright Taylor & Francis Group, LLC.
Wrodnigg, Tanja M.,Lundt, Inge,Stuetz, Arnold E.
p. 33 - 41
(2007/10/03)

Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
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(2008/06/13)

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Chemical Properties

Appearance/Colour :white crystalline solid
Melting Point: 182-185 °C (dec.)(lit.)
Boiling Point: 449.9 °C at 760 mmHg
Flash Point:225.9 °C
Density: 1.3965 (rough estimate)
Solubility:H2O: 50 mg/mL, clear, colorless
Storage Temp.:Store at 2-8
Vapor Pressure: 5.53E-10mmHg at 25°C
Refractive Index: 96 ° (C=1, H2O)
Sensitive: Hygroscopic
Merck: 14,4334
BRN: 3697825
PSA: 116.17000
LogP: -1.75270

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