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5 Carbohydrates
5.5
Amino-Sugars and Analogously Substituted Derivatives
Amino-sugars are systematically named as amino derivatives of the corresponding deoxy-sugars where an amino group replaces a hydroxy
group, also with respect to configuration. In the case of substitution at
position 2 mostly the trivial ... osamine names are preferred, e. g.:
trivially:
systematically:
o-Glucosamine
2-Amino-2-deoxy-o-glucose
0- Fucosamine
N-Acetyl-o-mannosamine
2-Amino-2,6-dideoxy-o-galactose
2-Acetamido-2-deoxy-0-mannose
Other non-terminal substituents are analogously accounted for, e.g.: 2deoxy-2-C-phenyl-o-glucopyranose; 2,3-diazido-2,3-dideoxy-0-mannopyranose; 3-deoxy-3,3-dimethyl-o-ribo-hexose etc. Substitution of an
aldehydic hydrogen is simply indicated by a C-substituent prefix: l-C-phenyl- o-glucose.
5.6
Transformations of the Carbonyl Functions
5.6.1
Oximes, Hydrazones, Osazones
Sugar derivatives obtained by replacing carbonyl oxygen with nitrogenlinked groups retain their traditional names.
HC=NOH
I
H-C-OH
I
H-C-OH
I
CH20H
0-Erythrose oxime
HC=N-NH2
I
H-C-OH
I
HO-C-H
I
H-C-OH
I
H-C-OH
I
CH20H
o-Glucose hydrazone
HC=N-NHPh
I
HC=N-NHPh
I
HO-C-H
I
H-C-OH
I
H-C-OH
I
CH20H
o-arabino-Hexos-2ulose bis(phenylhydrazone) (o-Fructose
phenyl osazone )