N-glycosides of 4-aminostyrene

Article abstract of DOI:10.1134/S1070363214020133

Glycosylation of 4-aminostyrene with α-D-glucopyranose, α,β-D-mannopyranose, L-rhamnopyranose, and α,β-L- arabopyranose in alcoholic medium has been studied. 4-Aminostyrene N-glycosides like 1-(4-vinylphenyl)amino-1-deoxy-D-glucopyranose, 1-(4-vinylphenyl

Full text of DOI:10.1134/S1070363214020133

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 2, pp. 235–241. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.L. Shul’tsev, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 2, pp. 242–248.
N-Glycosides of 4-Aminostyrene
A. L. Shul’tsev
Institute of High Molecular Compounds, Russian Academy of Sciences,
Bol’shoi pr. Vasil’evskogo Ostrova 31, St. Petersburg, 199004 Russia
e-mail: shultsev@list.ru
Received May 27, 2013
Abstract―Glycosylation of 4-aminostyrene with α-D-glucopyranose, α,β-D-mannopyranose, L-rhamno-
pyranose, and α,β-L-arabopyranose in alcoholic medium has been studied. 4-Aminostyrene N-glycosides like
1-(4-vinylphenyl)amino-1-deoxy-D-glucopyranose, 1-(4-vinylphenyl)amino-1-deoxy-β-D-mannopyranose, 1-(4-vinyl-
phenyl)amino-1-deoxy-β-L-rhamnopyranose, and 1-(4-vinylphenyl)amino-1-deoxy-L-arabopyranose were syn-
thesized and characterized for the first time.
DOI: 10.1134/S1070363214020133
Carbohydrate-containing polymers having saccharide
residues in the side chain and exhibiting valuable
properties, for instance, biological activity: immuno-
modulating [1], antitumor [2], etc., which are suitable
for preparation of new drugs and medical materials are
prepared mainly by homo- and copolymerization of
vinyl monomers, saccharides containing groups with
double carbon-carbon bonds in their structure. Among
these monomers esters and amides of unsaturated acids
are the most widespread, and more rarely the
unsaturated alcohol ethers are applied [3].
polyfunctional N-glycosides having in their structure
wide variety of saccharide residues in controlled ratio
and amounts, and exhibiting biological activity.
Hence, development of methods for preparation of
N-glycoside monomers from vinyl-containing amines
undoubtedly is an actual problem.
The aim of this work was the investigation of
glycosylation of 4-aminostyrene with α-D-glucopyra-
nose, α,β-D-mannopyranose, α-L-rhamnopyranose, and
α,β-L-arabopyranose in anhydrous alcoholic medium and
establishing the structure of the obtained N-glycosides.
At the same time practically no data concerning the
N-glycosides of vinyl-containing amines and no
descriptions of their synthesis are reported. The only
exclusions are short reports [4–6] and a paper [7]
describing glycosylation of allylamine and the struc-
ture of its N-glycosides. Creating of new group of
monomers opens new pathway to the synthesis of
Synthesis route of 4-aminostyrene N-glycosides:
1-(4-vinylphenyl)amino-1-deoxy-D-glucopyranose I,
1-(4-vinylphenyl)amino-1-deoxy-β-D-mannopyranose
II, 1-(4-vinylphenyl)amino-1-deoxy-β-L-rhamnopyranose
III, and 1-(4-vinylphenyl)amino-1-deoxy-L-arabopyranose
IV is presented in the scheme.
AlkOH, Δ
CH2
H2C
+ ROH
H2N
NH
R
H
OH
H
OH
H
H
CH3
O
O
O
HO
HO
OH
HO
OH
(I),
(II),
H
(III),
R =
H
H
H
H
HO
HO
OH
H
OH
H
H
H
H
H
H
H
O
OH
HO
(IV).
H
H
H
H
OH
235

236
SHUL’TSEV
Influence of parameters of the process on the yield of N-
glycoside II
Evidently in less concentrated starting alcoholic
solution of 4-aminostyrene the reaction proceeds faster
due to fast elimination of obtaining N-glycoside from
the surface of starting saccharide, and the excess of the
latter compensates the influence of lower concentration
of reacting substances due to the increase in the
specific surface. Therefore at the increased availability
of the D-mannose surface and its simultaneous growth
the reaction time decreases, and the yield of the
product significantly rises. Many monosaccharides are
insoluble in alcohols. In particular, α,β-D-mannose and
α-D-glucose are insoluble in anhydrous methanol and
ethanol even at boiling. Nevertheless, in the case of
glycosylation of 4-aminostyrene with α,β-D-manno-
pyranose the latter dissolves virtually completely
including the excess of monosaccharide. This un-
reacted monosaccharide does not crystallize from the
solution obtained after crystallization of the main part
of N-glycoside and its removal. No such effect was
observed in the glycosylation of allylamine.
Concentration of
Reaction
D-Mannose excess, 4-aminostyrene in
Yield,
%
time,
min
mol %
starting solution,
c×103, g/mL
0.005 (25.0)
0
79.43
230.00
111.77
30
53
13
52.0
19.3а
72.5b
0.0043 (21.6)
a
At the end of the process 1.3 mL of solvent was added, and the
reaction mixture was heated to boiling. The crystallized mass
b
was heated to boiling.
As is known, the rate of glycosylation depends on
the nucleophilicity of amine and the configuration of
the saccharide. Yield of N-glycosides significantly
depends also on the nature of reaction medium. In the
study of the glycosylation of aliphatic amines, for
example, allylamine, with aldohexoses in primary
aliphatic alcohols [7] it was found that the rate of the
reaction, the yield of target products, and the
occurrence of by-processes under the other equal
conditions strongly depend on the nature of alcohol. It
was shown also that hexoses containing equatorial
hydroxy group in the position 4 demonstrate the
highest reactivity.
At treating pure 4-aminostyrene with α-D-gluco-
pyranose in alcoholic medium no glycosylation occurs.
For example, heating a mixture of reagents under the
inert atmosphere at 70°C in anhydrous methanol or its
mixture with anhydrous ethanol for 4–5 h only
dissolution of major part of starting monosaccharide
and its anomerization were observed. From the solu-
tion of reaction mixture besides the starting amine only
the mixture of anomers of D-glucopyranose was
always isolated. β-Anomer is formed in the amounts
comparable with α-anomer. These results were
obtained while performing at least ten experiments
with starting solutions of different composition. Hence,
the change in the relative configuration of mono-
saccharide, in this case in going from the axial location
of hydroxyl at C2 to the equatorial one its reactivity
decreases. The same effect was observed in the
glycosylation of allylamine [7]. The mechanism of
formation of stable oversaturated alcoholic solutions of
D-mannopyranose in the course of the synthesis of N-
glycoside II or of α,β-D-glucopyranose in the course
of isomerization of α-anomer is not sufficiently clear,
but it may be suggested that it is similar in both cases.
4-Aminostyrene, the aromatic amine, has
significantly lower nucleophilicity than the aliphatic
primary amines. Therefore it is presumable that it is
would be less reactive towards the saccharides. But it
has been shown in the investigation of its glycosylation
with monosaccharides in alcohols that one of the main
factors influencing the process is the configuration of
the saccharide, and not the nucleophilicity of the amine.
For example, the reaction of α,β-D-mannopyranose
with 4-aminostyrene proceeds as easily as with
allylamine, but unlike the latter case, the yield of N-
glycoside is strongly affected by the excess of
monosaccharide.
It was found that under other equal conditions 4-
aminostyrene can undergo glycosylation with D-
glucose simultaneously with 1-amino-4-ethylbenzene.
For example, heating a mixture containing 70 mol %
of 4-aminostyrene and 30 mol % of 1-amino-4-
ethylbenzene together with D-glucopyranose in a
mixture of anhydrous methanol and ethanol at 70°C
As seen from the table, at stoichiometric ratio of
reagents a low yield of the product is observed even at
their higher concentration. Higher yield of 1-(4-
vinylphenyl)amino-1-deoxy-β-D-mannopyranose is ob-
tained at the excess of α,β-D-mannopyranose and in
reaction proceeding in a large amount of solvent.
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N-GLYCOSIDES OF 4-AMINOSTYRENE
δ, ppm
Fig. 1. 1H NMR spectrum of N-glicoside II.
for 5 h leads to the formation of two N-glycosides
among which 1-(4-vinylphenyl)amino-1-deoxy-D-gluco-
pyranose I is the prevailing product.
13C NMR spectrum (Fig. 2) unambiguously shows
that this compound is present as one anomer, has a six-
member heteroring, and in the course of glycosylation
no formation of admixtures of other isomers occurs.
Signals of the pyranose ring carbon atoms C2–5 are
located in the upfield region. The signal corresponding
to the exocyclic atom C6 is observed at δC 63.10 ppm.
The signal of the anomeric atom C1 is located at 83.05 ppm,
and in the range 114–149 ppm the set of signals of
aglycone appears. Signals of carbon atoms in the
positions 3, 4, and 5 of the aromatic ring overlap and
give two peaks at 128.04 and 128.30 ppm respectively.
Structure of N-glycosides I-IV was established
1
using H and 13C NMR spectroscopy including cor-
relation methods HSQC and HMBC. Relative
configuration of compounds at the anomeric C1 atom
was established from the value of JH –H coupling
1
2
1
constant in the H NMR spectrum. The signal of the
corresponding H1 atom was found from the cross-peak
belonging to the coupling of 1H1 and 13C1 nuclei.
NMR spectra confirming the structure of 1-(4-
vinylphenyl)amino-1-deoxy-β-D-mannopyranose are
presented in Figs. 1−3.
In the reaction of 4-aminostyrene with L-
rhamnopyranose and L-arabinose no complications are
observed. In the case of L-rhamnose N-glycoside III is
formed in good yield. From the spectral data presented
in Fig. 3 it follows that this compound also exists in
the pyranose form.
In the 1H NMR spectrum (Fig. 1) signals of protons
of D-mannose residue are located in the range 3.2–
4.9 ppm. H1 anomeric proton is characterized by a
doublet of doublets at 4.87–4.89 ppm (J 9.4 Hz). High
value of coupling constant JH1–H2 shows that the
anomeric center of saccharide II has β-configuration.
Signal of the vinyl group protons appear in the range
4.9–6.7 ppm. Geminal protons give two doublets at
4.9–5.7 ppm, and vicinal proton is characterized by a
quartet at 6.63 ppm. Doublet of the proton of
secondary amino group is observed at 6.11 ppm
(J 9.4 Hz). Two intense downfield doublets belong to
the protons of the aromatic ring.
In the 13C NMR spectrum a set of signals of C1–5
carbon atoms appears in the range 71–84 ppm. The
signal of the anomeric proton H1 gives a doublet of
doublets at 4.88-4.91 ppm (J 9.8 Hz), consequently the
anomeric center of the saccharide III has also β-
configuration. The exocyclic atom C6 is characterized
by an upfield signal. The other cross-peaks excluding
the signals of solvent correspond to the coupling of 1H
and 13C atoms of aglycone.
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238
SHUL’TSEV
δ, ppm
Fig. 2. 13C NMR spectrum of N-glycoside II in DMF-d7.
Нcis
Нtrans
δ, ppm
Fig. 3. HSQC 1H–13C NMR spectrum of 1-(4-vinylphenyl)amino-1-deoxy-β-L-rhamnopyranose (DMF-d7).
In the course of the reaction of 4-aminostyrene with
conclusion that the product of glycosylation may exist
as β-anomer of N-arabinopyranoside IV as well as a
mixture of isomers including its α- and β-anomers
containing the admixture of furanose forms. The trend
α,β-L-arabinose in anhydrous methanol several
isomers of N-glycoside are formed. Analysis of HSQC
NMR data, in particular, 13C NMR spectra, permits a
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239
N-GLYCOSIDES OF 4-AMINOSTYRENE
in N-arabinoside to form several isomers is evidently
due to the absence of substituent at C5 atom of the
carbohydrate part of the molecule.
substance was obtained. All filtrates were combined,
and the solvent was removed in a vacuum. The syrup-
like residue was treated with 50 mL of anhydrous
diethyl ether, and fine crystalline precipitate began to
form. The suspension was decanted, the hygroscopic
residue was quickly filtered off, washed with an-
hydrous diethyl ether, and immediately placed in a
vacuum dessicator over P4O10. The residue was
triturated in the anhydrous diethyl ether, the obtained
suspension was filtered off, the crystals were washed
with anhydrous diethyl ether and dried in a vacuum
over P4O10. A mixture of N-glycosides was obtained as
a fine crystalline powder, yield 0.60 g, mp 80.5–83°C.
It contained 53.4 mol % of N-glycoside I. From the
obtained mixture 1-(4-vinylphenyl)amino-1-deoxy-D-
glucopyranose was isolated by column chromato-
Hence, the process of glycosylation of 4-amino-
styrene with aldoses was investigated, and it was found
that most reactive are saccharides having the equatorial
location of hydroxy group on C4 and axial on C2 atom.
The presence of substituent at C5 influences the stab-
ility of carbohydrate part of molecule and its
configuration. The interaction of starting substances,
intermediates, reaction products, and solvent with one
another is observed. It is expressed in such effects, as
glycosylation proper, in particular, with D-glucose,
anomerization of starting monosaccharides and their
unusual solubility. Finally note that 1-(4-vinylphenyl)-
amino-1-deoxy-D- and L-saccharides, synthesized and
characterized for the first time, are successfully used as
new vinyl monomers.
1
graphy. H NMR spectrum (D2O), δ, ppm: 3.35–4.75
m (11H, H1–6, OH2–4,6), 4.5–7.0 d (1H, NH), 5.10 d.d
(1H, cis-H, J 11.1 Hz), 5.54 d.d (1H, vic-H, J 11.0 Hz),
6.82 d (2H, 2,6-Ar, J 8.4 Hz), 7.35 d (2H, 3,5-Ar,
J 8.5 Hz).
EXPERIMENTAL
NMR spectra were registered on a Bruker Avance
1
II 400 spectrometer (400.1 MHz H, 100.6 MHz 13C)
1-(4-Vinylphenyl)amino-1-deoxy-β-D-manno-
pyranose II. a. To a solution of 2.383 g (20 mmol) of
4-aminostyrene in 30 mL of anhydrous methanol 4.504 g
(25 mmol) of finely powdered α,β-D-mannopyranose
was added. The reaction mixture was heated under
argon for 0.5 h at 70°C with intermittent stirring. The
most part of D-mannose dissolved in the course of 13–
15 min, and at the end of heating the dissolution was
almost complete. The solution was decanted from the
insignificant amount of precipitate and left for
crystallization. After several minutes the crystals
formed were filtered off, washed with small amount of
methanol, and dried over P4O10. N-glycoside, 2.45 g,
was obtained as lustrous plate crystals. The rest of the
product was extracted at heating with small amounts of
methanol, insoluble precipitate was filtered off, and
combined filtrates were concentrated in a vacuum.
Fine crystalline precipitate was filtered off, washed
with methanol, and dried to give 0.45 g of product II.
One more portion of crystals, 0.13 g of white fine
crystalline substance was isolated from the filtrate.
This batch was crystallized from boiling methanol to
give 0.025 g of N-glycoside. Total yield 2.925 g
(52%). TLC: Rf 0.72. 1H NMR spectrum, δ, ppm: 3.35
m (1H, H5), 3.5–4.0 m (9H, H2–4,6, OH2–4,6), 4.88 d.d
(1H, β-H1, J 0.8, J 9.4 Hz), 4.98 d.d (1H, cis-H, J 1.1,
J 10.9 Hz), 5.58 d.d (1H, trans-H, J 1.2, J 17.6 Hz),
6.11 d (1H, NH, J 9.4 Hz), 6.63 q (1H, vic-H, J
11.0 Hz), 6.84 d (2H, 2,6-Ar, J 8.6 Hz), 7.28 d (2H,
in DMF-d7 (δ 8.03 ppm, CDO), and in D2O (δ 4.78 ppm,
HDO suppression). UV spectra were registered on a
LOMO SF-256 UVI spectrophotometer. Elemental
analysis data were obtained on a Vario Elemental
C,H,N,S analyzer. TLC was carried out on Silufol UV
254 plates (elution with MeOH, development with I2).
Anhydrous methanol and ethanol were prepared by
treating commercial product with excess CaH2,
distillation, and repeated distillation with small amount
of sodium. Diethyl ether was purified from admixtures
and boiled over sodium. Anhydrous monosaccharides
of “chemically pure” grade were used. Synthesis of
starting 4-aminostyrene was described previously [8–12].
1-(4-Vinylphenyl)amino-1-deoxy-D-glucopyranose
I. A mixture, 0.33 g, of 4-aminostyrene (70 mol % or
69.9 wt %, 1.9 mmol) with 1-amino-4-ethylbenzene
(30 mol %), was treated with 0.001 g of hydroquinone,
0.005 g of sodium bisulfite, 2.5 mL of anhydrous
methanol, 2.5 mL of anhydrous ethanol, and 0.75 g of
finely pulverized α-D-glucopyranose. After that the
reaction mixture was heated under argon at 70°C for
5 h with intermittent stirring. After the reaction was
complete the solution was decanted from the
precipitate of D-glycose, and the suspended material
was filtered off. The residual D-glucose was twice
washed with anhydrous ethanol, and then with
anhydrous diethyl ether. After drying in air 0.23 g of
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240
SHUL’TSEV
13
3,5-Ar, J 8.6 Hz). C NMR spectrum, δC, ppm: 63.10
(C6), 68.98 (C4), 72.74 (C3), 76.30 (C2), 79.25 (C5),
83.05 (C1), 109.75 (=CH2), 114.75 (2,6-Ar), 128.05
(3,5-Ar), 128.31 (3-Ar), 138.03 (CH=), 147.76 (1-Ar).
UV spectrum, λmax, nm: 274.9 (H2O); 278.9 (MeOH).
Found, %: C 59.29, H 6.92. C14H19NO5. Calculated, %:
C 59.78, H 6.81.
filtered off, washed with small amount of cooled
anhydrous methanol and dried in air, and then in a
vacuum over P4O10. Yield 1.64 g (56.3%), white
crystalline substance decomposing while heating. TLC:
1
Rf 0.72. H NMR spectrum, δ, ppm: 1.21 t (3H, CH3,
J 5.8 Hz), 3.3–3.6 m (6H, H3–5, OH3–5), 3.92 d (1H, H2,
J 2.6 Hz), 4.90 d.d (1H, βH1, J 0.6, J 9.8 Hz), 4.98 d.d
(1H, cis-H, J 1.0, J 10.9 Hz), 5.57 d.d (1H, trans-H,
J 1.1, J 17.6 Hz), 5.96 d (1H, NH, J 9.8 Hz), 6.63 q
(1H, vic-H, J 11.0 Hz), 6.83 d (2H, 2,6-Ar, J 8.6 Hz),
Filtrate obtained after isolation of the product was
diluted with the excess of diethyl ether. White viscous
precipitate was formed which crystallized in air. Yield
1.90 g. It was identified as a mixture of D-manno-
pyranose and N-glycoside II in 10 : 1 ratio.
13
7.28 d (2H, 3,5-Ar, J 8.6 Hz). C NMR spectrum, δC,
ppm: 18.68 (C6); 72.81 (C2); 73.84, 76.05 (C3–5), 82.55
(C1), 109.77 (=CH2), 114.80 (2,6-Ar), 128.06 (3,5-Ar),
128.34 (4-Ar), 138.02 (CH=), 147.78 (1-Ar) UV
spectrum (H2O), λmax, nm: 275.9.
b. To a solution of 1.38 g (11.6 mmol) of 4-amino-
styrene in 6 mL of anhydrous methanol 2.09 g
(11.6 mmol) of α,β-D-mannopyranose was added. The
reaction mixture was stirred and heated for 53 min at
70°C under argon with intermittent stirring. After that
1.3 mL of anhydrous methanol was added, reaction mix-
ture was heated to boiling and left for crystallization.
When the crystallization was complete, the solid
obtained was filtered off, washed twice with small
portions of anhydrous methanol, and dried over P4O10.
Yield 0.63 g (19.3%), white crystalline substance. UV
spectrum (H2O), λmax 274.9 nm. From the filtrate 1.1 g
of contaminated D-mannopyranose was isolated.
1-(4-Vinylphenyl)amino-1-deoxy-L-arabinopyra-
nose IV. a. A mixture of 0.08 g (0.67 mmol) of 4-
aminostyrene, 1.0 mL of anhydrous methanol, and
0.10 g (0.67 mmol) of α,β-L-arabinose was heated at
69–70°C for 65 min under intermittent stirring. After
that the insignificant amount of unreacted mono-
saccharide was filtered off and washed with anhydrous
methanol. The filtrate was added to 50 mL of
anhydrous diethyl ether, the obtained solution was
evaporated in a vacuum, and the residue was several
times washed with anhydrous diethyl ether. After that
the residue was crushed under a layer of anhydrous
diethyl ether, filtered, and dried over P4O10. Yield 0.05 g
(29.7%), white crystalline hygroscopic substance
melting and acquiring coloration in air. UV spectrum
(MeOH), λmax, nm: 200, 279.9.
c. To a solution of 4-aminostyrene (1.90 g, 15.9 mmol)
in 17 mL of anhydrous methanol 3.59 g (19.9 mmol)
of α,β-D-mannopyranose was added. The obtained
mixture was heated to 69°C with intermittent stirring
for 13 min. During this period dissolution of D-
mannose and subsequent crystallization of N-glycoside
was observed. The obtained reaction mixture was
heated to boiling, and after cooling the product was
filtered off, twice washed with cooled anhydrous
methanol, and dried in air. Residual D-mannose was
boiled with filtrate, hot solution was decanted from the
insoluble precipitate which was washed with an-
hydrous methanol, and all liquids were combined.
After crystallization additional portion of the product
was obtained. Total yield 3.25 g (72.5%).
b. A solution of 1.70 g (14.3 mmol) of 4-amino-
styrene in 8 mL of anhydrous methanol was heated to
65°C, and 2.25 g (15.0 mmol) of pulverized α,β-L-
arabinose was added to it. After that it was heated
under argon at 69°C for 39 min. The isolation of the
product was carried out analogously to the previous
case. The syrup obtained after removing solvents was
crystallized by triturating it on a glass with intermittent
washing with anhydrous diethyl ether. Yield 2.76 g
13
(77%). C NMR spectrum (DMF-d7), δC, ppm: 66.63
(C5); 69.45, 71.89, 74.98 (C2-4); 86.41 (βC1), 109.58
(=CH2), 114.39 (2,6-Ar), 128.01 (3,5-Ar), 128.10 (4-
Ar), 137.99 (CH=), 148.44 (1-Ar).
1-(4-Vinylphenyl)amino-1-deoxy-β-L-rhamno-
pyranose III. To a solution of 1.31 g (11.0 mmol) of
4-aminostyrene in 2.0 mL of anhydrous methanol
heated to 65°C 2.05 g (12.5 mmol) of finely pulverized
α-L-rhamnopyranose was added. The reaction mixture
was heated under argon at 65±0.5°C for 54 min. After
45 min of heating the solution began to crystallize, and
at the end of heating the reaction mixture solidified.
The obtained solid mass was crushed, the crystals were
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