5.11 Monosaccarides as Substituent Groups
HC=O
I
H-C-O
I
\
HO-C-H CH 2
I
/
H-C-O
HO~CH2~ H
OH H
H
0 H
\ /
/O-CH2
Me2C,
I
O-C-H
I
HO-C-H
169
I
CH20H
H O-C,
Ph
I
H-C-OH
I
H-C-O
I
~CMe2
H 2 C-O
2,4-0-Methylenexylose
1,2-0-BenzylideneD-glucofuranose
1,2: S,6-Di-0-isopropylidene-D-mannitol
5.11
Monosaccharides as Substituent Groups
If need arises, five types of substituent groups can be derived from sugars
and their derivatives, whose names are formed by supplementing the
group suffix ... osyl with suitable descriptors.
a) the free valence is generated through detachment of the anomeric
hydroxy group: ... osyl. These are the prototypical glycosyl groups
found in the general literature (see also the next section).
b) the free valence at C-l is generated while keeping the hydroxy group in
place: I-hydroxy ... osyl.
c) a free valence is generated at any (non-anomeric) C atom bearing a
hydroxy group: ... os-n-C-yl.
d) a free valence is generated at any (non-anomeric) hydroxy group: ... osn-O-yl.
e) the free valence is generated at a reduced center: n-deoxy ... os-n-yl.
OH
H
NHAc
a) 2-(2-C-Acetamido-2,3,4,6tetra-O-acetyl-f3-D-manno
pyranosyl)phenol
N~
H2N~N
N~ NH
HOH2 C
W,
H H
H
H
OH H
a) 8-(2-Deoxy-f3- D-erythropentofuranosyl)adenine