Synthesis and schematic mechanism of 3-phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside

Article abstract of DOI:10.14233/ajchem.2018.21472

A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidine (acetylated glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II). Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-α-D-glucopyranosyl bromide (III). In step 3 compound (III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-β-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectroscopy.

Full text of DOI:10.14233/ajchem.2018.21472

Asian Journal of Chemistry; Vol. 30, No. 10 (2018), 2310-2316
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2018.21472
Synthesis and Schematic Mechanism of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-
glucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside
1
ARUNA HARDAS and PRITI TAYADE (GOSAVI)2,*
1Department of Chemistry, S.F.S. College, Seminary Hills, Nagpur-440 006, India
2Innovation Hub, Raman Science Centre, Nagpur-440 018, India
*Corresponding author: E-mail: gosavipriti@gmail.com
Received: 24 May 2018;
Accepted: 3 July 2018;
Published online: 31 August 2018;
AJC-19064
A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidine (acetylated
glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II).
Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-α-D-glucopyranosyl bromide (III). In step 3 compound
(III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-
O-acetyl-β-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro
isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl
nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-β-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated
glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono
nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance
spectroscopy and mass spectroscopy.
Keywords: Glucopyranosylimino nucleoside, Mass spectroscopy, IR spectroscopy.
Various synthetic nucleosides such as 2-tetra-O-benzoyl-
β-D-glucopyranosyl-4-phenyl-5-arylimino-1,3,4-thiadiazo-
lidines [7], substituted 2-amino-(6-substituted)benzo-1,3-
thiazoles [8] and benzoylated glucopyranosyl disubstituted
thiocarbamide [9], etc. have been reported. However, open
access literature is lacking in detail synthesis route.
Other than this reported route, synthetic nucleosides can
be prepared by interaction of S-chloro-N-phenyl isothio-
carbamoyl chloride and 1-phenyl-3-tetra-O-acetyl-β-D-gluco-
pyranosyl thiocarbamides. Further de-acetylating process
results into the corresponding hydroxylated nucleoside.
Present paper describes the stepwise synthesis of 3-
phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyrano-
sylimino-1,3,4-dithiazolidine from glucose as starting material.
Furthermore, de-acetylating process result into actual required
glucospyranosylimino nucleoside. 3-Phenylimino-4-phenyl-
5-tetra-O-acetyl-β-D-glucopyranosylimino-1,3,4-dithia-
zolidine is broadly referred as acetylated glucopyranosylimino
nucleoside. Similarly, 3-phenylimino-4-phenyl-5-tetra-
INTRODUCTION
Broadly speaking nucleosides are glycosylamine which
can be converted to nucleotides i.e. having phosphate group
[1]. The major constituents of nucleoside are nitrogenous base
and ribose or de-oxyribose. The base in nucleoside is connected
to ribose or de-oxyribose through β-glycosidic linkage [2].
Some naturally occurring nucleosides are cytidine, uridine,
adenosine, guanosine, thymidine and inosine etc. [3,4]. How-
ever, there is need of synthetic nucleoside analogues in order
to arrest viral growth, cancer cell growth and for some other
related medicinal issues. The benefit of using synthetic nucleo-
side is that, these compounds after administration get activated
in cells and get converted into its active nucleotides. Usually
nucleotides are charged and don’t cross the cell membrane
easily, which can be easily done by using nucleoside [5]. These
synthetic nucleosides also work as sugar backbone and does
not hydrolyse as easy as RNA, hence, provides the stability in
such cases [6].
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Vol. 30, No. 10 (2018)
Synthesis of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines 2311
hydroxyl-β-D-glucopyranosylimino-1,3,4-dithiazolidine is
broadly referred as de-acetylated glucopyranosylimino
nucleoside.
The work also elucidates the mechanistic scheme for both
acetylated and de-acetylated glucopyranosylimino nucleosides
by using mass spectrometry.
Synthesis of acetylated nucleoside from glucose
Preparation of glucose pentaacetate: The synthesis
method opted for synthesis of glucose pentaacetate is reported
by Huang et al. [15]. In the particular process 40 mL of an ice
cold acetic anhydride was added to 0.25 mL perchloric acid.
The resultant pale yellow coloured solution was added gradu-
ally to 10 g of D glucose with constant shaking. The reaction
mixture was kept without disturbing for 15 min at room tempe-
rature. The solution was precipitated out in ice cold water. The
precipitate is of glucose pentaacetate. Glucose pentaacetate
was crystallized in methanol. Presence of glucose pentaacetate
was confirmed by observing melting point 110 °C (Scheme-
IV).
EXPERIMENTAL
All the precursor chemicals namely, glucose, ethanol,
methanol, acetic anhydride, acetic acid, benzene, chloroform,
xylene, carbon tetrachloride, red phosphorus were obtained from
make E-Merck.
Synthesis of acetylated nucleoside i.e. 3-phenylimino-4-
phenyl-5-tetra-oacetyl β-D-glucopyaranosyl imino-1,2,4-
dithiazolidine was carried out from glucose as starting material.
Furthermore acetylated nucleoside is de-acetylated to the actual
nucleoside.
Synthesis of brominating reagent: The brominating
reagent was prepared by using Hell-Volhard-Zelinsky process.
In the particular process, 30 mL of glacial acetic acid was taken
in conical flask and 3 g of red phosphorous was added. To this
mixture 7 mL of molecular bromine was added gradually with
constant shaking and cooling. The resultant mixture was allowed
to stand for 15 min at room temperature [10,11]. The solution
was then filtered through cotton filter in order to remove
suspended impurities (Scheme-I).
O
CH3
O
OH
O
O
O
O
H
H
O
H
H
CH3
CH3
HClO4
H
H
O
+
O
H3C
OH
H
H
O
O
HO
OH
O
O
H
OH
O
CH3
H
H3C
O
CH3
Scheme-IV: Reaction step-I
Synthesis of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl
bromide: 21.6 g of glucose pentaacetate was added to the
brominating reagent. The resultant solution was kept undis-
turbed at room temperature for 2 h. The reaction mixture was
mixed with 30 mL of carbon tetrachloride with vigorous shaking
for 15 min. The resultant mixture was poured in to the ice-
cold water. The carbon tetrachloride is separated out from
product. The product was washed several times with sodium
bicarbonate to remove excess of glacial acetic acid. Similarly,
product was also washed by sodium meta-bisulphide to remove
excess of bromide. Finally product was washed with water
several times. The layer of carbon tetrachloride was then dried
over anhydrous calcium chloride. The solvent was removed
through vacuum distillation to obtain the solid tetra-o-acetyl-
α-D-glucopyranosyl bromide. The product is crystallized from
petroleum ether and confirmed by melting point as 88 °C [16]
(Scheme-V).
O
OH
Br
O
Br Br
Red P
+
+
H C
3
OH
Scheme-I: Synthesis of reagent-I
Synthesis of lead isothiocyanate: Lead nitrate (33 g)
solution was mixed with 15 g of ammonium thiocyanate. The
white coloured granular lead thiocyanate was obtained. The
granules were filtered and washed with distilled water and
dried in an oven at 50 °C [12] (Scheme-II).
Pb(NO3)2 + 2(NH4SCN) → Pb(SCN)2 + 2NH4NO3
Scheme-II: Synthesis of reagent-II
O
CH3
O
CH3
Synthesis of N-pheyl-S-chloro isothiocarbamoyl chloride:
A solution of 7 mL phenyl isocyanate in 15 mL of chloroform
was prepared. Chlorine gas generated from 3.2 g of potassium
permangante and 20 conc. HCl was bubbled while maintaining
temperature below 10 °C [13]. After addition of chlorine the
reaction mixture turned to yellow colour. This yellow reaction
mixture was diluted with 40 mL dry petroleum ether. The solvent
was removed by dry distillation under vacuum. The whole
process of distillation is repeated till we obtained pale yellow
oil of N-phenyl-S-chloro isothiocarbamoyl chloride (Scheme-
III) [14].
O
O
O
O
O
O
H
H
H
H
O
OH
H
Brominating agent
CCl4
H
H3C
H3C
O
H
H
+
O
O
O
Br
Br
O
O
O
H
O
CH3
H
O
O
H3C
H3C
O
O
CH3
CH3
Glucose pentacetate
2,3,4,6-tetra-acetyl-
glucopyranosyl bromide
α
-D-
Scheme-V: Reaction step-II
Synthesis of 2,3,4,6-tetra-o-acetyl β-D-glucopyranosyl-
isothiocyanate: A solution of 20 g of tetra-O-acetyl-α-D-
glucopyranosyl bromide in 150 mL xylene was prepared.
To this solution 16 g of lead isothiocyanate was added. The
reaction mixture was refluxed for 3 h with frequent shaking.
The solution was allowed to cool and separated out by filtration
from lead bromide [9,17]. The xylene filtrate was added to
O
N
Cl
Cl
N
Chloroform KMnO4 and con.HCl
S
Scheme-III: Synthesis of reagent-III

2312 Hardas et al.
Asian J. Chem.
petroleum ether result into solid product with yield of 14 g.
The product was purified by dissolving it in minimum quantity
of ethanol and re-precipitated by water. The product was con-
firmed by melting point (112-114 °C) (Scheme-VI).
by adding 9.6 g of powdered N-phenyl-2,3,4,6-tetra-O-acetyl-
β-D-glucupyranosyl thiocarbamide into 40 mL benzene was
prepared. To another flask, solution of 4.12 g of N-phenyl-S-
chloro isothiocarbamoyl chloride was added to 20 mL benzene
to form solution. The prepared suspension and solution were
mixed and refluxed over boiling water bath for 4 h. While
reflux brisk reaction takes place with the evolution of HCl
and gradual conversion of solid into solution. After refluxing
the solution was filtered to remove suspended particle. After-
wards solvent was distilled off. An oily residue was obtained,
which was triturated with petroleum ether followed by ethanol.
A pale yellow solid was obtained which was crystallized in
aqueous ethanol (m.p. 199 °C) (Scheme-VIII).
O
CH3
O
CH3
O
O
O
O
O
O
H
H
H
N
H
S
H
O
H
O
Pb(SCN)
H3C
2
H3C
+
H
H
O
O
Br
O
O
O
H
O
H
H3C
H3C
O
O
CH3
CH3
2,3,4,6
2,3,4,6 tetra-O-acetyl-β−
D
tetra-O-acetyl-α−D-glucopyranosyl
glucopyranosyl isothiocynate
bromide
De-acetylating 3-phenylimino-4-phenyl-5-tetra-o-
acetyl-β-D-glucopyranosyl imino-1,2,4-dithiazolidine: 2 g
of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyra-
noyl imino-1,2,4-dithiazolidine was suspended in 35 mL pure
methanol. To this suspension 4 mL of liquor ammonia was
added. The reaction mixture was kept in an ice bath and stirred
magnetically for 6 h. Gradually solid dissolved to form solution.
The reaction solution was allowed to left overnight. The solvent
residue was removed by distillation. The obtained product was
allowed to treat with methanol to obtain final product [18].
The product was crystallized by using ethanol. The yield of
product was 1.2 g i.e. 82 % (Scheme-IX).
Scheme-VI: Reaction step-III
Synthesis of N-phenyl-2,3,4,6-tetra-O-acetyl-β-D-
glucopyranosyl thiocarbamide: 0.02 M i.e. 7.8 g of 2,3,4,6-
tetra-O-acetyl-β-D-glucopyronosyl isothiocyanate was dissol-
ved in 50 mL benzene. In another flask solution of 1.8 g of
aniline in 10 g of benzene was prepared. Both the solutions
were mixed and allowed to reflux over boiling water bath for
3 h.After refluxing with said conditions benzene was removed
by distillation. A sticky mass was obtained as residue, which
was triturated several times with petroleum ether. A granular
solid with yield of 6.5 g was obtained. The product was crysta-
llized from aq. ethanol (m.p. 162 °C) (Scheme-VII).
The product was confirmed by several methods such as
melting point, elemental analysis, UV, IR, NMR and mass
spectra.
Synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-
β-D-glucupyranosyl imino-1,2,4-dithizolidine:A suspension
O
H
CH3
O
O
H
CH3
O
O
NH2
O
H
N
H
S
S
H
N
O
O
H
Benzene
H3C
NH
H
O
+
H3C
H
O
H
O
O
H
O
O
H3C
O
H
O
O
H3C
CH3
O
CH3
2,3,4,6 tetra-O-acetyl-β−
D
N-phenyl-2,3,4,6
glucopyranosyl isothiocynate
tetra-O-acetyl-β−D-glucopyranosyl
thiocarbamide
Scheme-VII: Reaction step-IV
O
CH
O
3
O
H
CH
3
O
O
S
H
N
O
C
H
N
NH
NH
Cl Benzene
Cl
N
O
H
O
O
+
H
H
C
S
3
N
H
H
O
S
H
S
H C
3
H
O
O
O
H
O
H
3
O
H
O
O
H C
3
CH
3
O
CH
3
3-phenylimino-4-phenyl-tetra
-O-acetyl-β−D-glucopyranosyl
imino-1,2,4 -dithiazolidone
N-phenyl-S-chloro-isothiocarb
amoyl
N-phenyl-3-tetra-O-acetyl-β−D-
glucopyranosyl thiocarbamide
Scheme-VIII: Reaction step-V

Vol. 30, No. 10 (2018)
Synthesis of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines 2313
O
CH3
O
N
NH
O
O
H
OH
S
N
H
H
S
H3C
N
NH
H
O
O
H
Methanol
S
N
H
O
H
S
H
OH
H
O
H
Liq ammonia
HO
O
H3C
O
CH3
OH
Acetylated glucopyranosylimino
nucleosidde
De-acetylated glucopyranosylimino
nucleoside
(Yield 65 %, m.p. 199 °C)
(Yield 82 %, m.p. 194 °C)
Scheme-IX: Reaction step-VI
RESULTS AND DISCUSSION
The specific rotation [α]D30 of acetylated glucopyranosyl-
imino nucleoside was found to be +199 (0, 0.94) in chloroform.
The specific rotation [α]D30 of de-acetylated product in methanol
was recorded to be -96.53 (0, 0.13).
The acetylated glucopyranosylimino nucleoside was
insoluble in water. However, it was soluble in organic solvents
such as benzene, ethanol, chloroform and acetone. The de-
acetylated glucopyranosylimino nucleoside was soluble in
methanol and ethanol.
Effect of conc. H2SO4: The obtained solid product was
placed in a China dish and concentrated H2SO4 was dropped
onto it. In the next turn same procedure was followed for de-
acetylated product. According to the observation, acetylated
and de-acetylated both the products got charred when treated
with conc. H2SO4.
Fig. 1. UV spectra for 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-
glucopyranosylimino-1,2,4-dithiazolidone
Effect of alkaline plumbite solution: Alkaline plumbite
solution was added to the both acetylated nucleoside and de-
acetylated nucleoside separately and boiled to observe release
of sulphur. According to the observations, both the products
i.e. acetylated and de-acetylated glucopyranosylimino
nucleoside was found to be non-de-sulphurizable when boiled
with alkaline plumbite solution. Which implies sulphur is
present in the ring, which could not be released by boiling
with alkaline plumbite solution.
Acetylated and de-acetylated glucopyranosylimino
nucleosides were allowed to decompose thermally. Perceptible
odour of phenylisocyanate was observed.
Elemental analysis of acetylated glucopyronosylimino
nucleoside was found to be C = 55.49, H = 4.81, N = 6.87, S
= 10.10 corresponding to the m.f. C28H29N3O9S2. The elemental
compositions (%) were anticipated to be, C = 55.63, H = 4.71,
N = 6.82, S = 10.24.
For de-acetylated glucopyranosylimino nucleoside was
found to be; C = 53.79, H = 4.76, N = 9.35, S = 13.47. The
molecular formula estimated from this was C20H21O5N3S2. The
elemental analysis was found to be very close to expected
numbers i.e. C = 53.69, H = 4.69, N = 9.39, S = 13.21 by
percentage.
The UV spectrum of the acetylated glucopyranosylimino
nucleoside was observed at λmax of 240 nm in chloroform
shown in Fig. 1. UV spectrum of de-acetylated glucopyrano-
sylimino nucleoside was recorded at λ max of 210 nm is shown
in Fig. 2.
Fig. 2. UV spectra for 3-phenylimino-4-phenyl-5-tetra-hydroxy-β-D-
IR spectral peaks for acetylated and de-acetylated gluco-
pyranosylimino nucleoside are listed in Table-1.
glucopyranosylimino-1,2,4-dithiazolidone

2314 Hardas et al.
Asian J. Chem.
TABLE-1
The NMR spectrum of acetylated glucopyranosylimino
nucleoside shows the signals due to aromatic proton were
observed at δ 6.80 to δ 7.30 ppm. The signal due to acetyl
proton was observed at δ 2.05 ppm. Signals due to pyranosyl
ring was observed at δ 3.5-4.2 ppm and 4.75-5.25 pmm.
The NMR spectrum of de-acetylated glucopyranosylimino
nucleoside shows a signal at 6.5-7.3 ppm due to aromatic
protons. β-D-glucopyranosyl ring protons at δ of 2.5-3.2 ppm.
Signal at δ of 4-5 ppm was observed which are responsible
for OH protons.
IR ADSORPTION PEAK FOR ACETYLATED
GLUCOPYRANOSYLIMINO NUCLEOSIDE AND DE-
ACETYLATED GLUCOPYRANOSYLIMINO NUCLEOSIDE
Adsorption (cm-1)
Adsorption corresponding group
IR adsorption bands for acetylated glucopyranosylimino nucleoside)
1750
1610
1330
690
C=O stretching
C=N stretching
C-N stretching
C-S stretching
480
S-S stretching
Mass spectra: The mass spectra of acetylated and de-
acetylated glucopyranosyl nucleosides were recorded by using
‘Thermo LCQ Advantage Max Ion Trap Mass spectrometer’
(ESI-MS, APCI-MS and LC-MS/MS).
The spectra of acetylated glucopyranosylimino nucleo-
side shows the protonated molecular ion peak along with other
important fragment peaks with their relative abundances are
listed in Table-2. The probable fragmentation pattern of mole-
cular ion are shown in Scheme-X of mechanism.
898
Glycosidic C-H deformation-β-anomer
Adsorption bands for de-acetylated glucopyranosylimino nucleoside)
3520
1580
1280
690
500
890
O-H stretching
C=N stretching
C-N Stretching
C-S stretching
S-S stretching
Glycosidic C-H deformation-β-anomer
OAc
Ph
+
OAc
H
Ph
N
Ph
.
N
N
Ph
N
O
H
S
O
N
H
H
-CH3COOH
S
N
H
S
S
OAc
H
(m/e)=496
protonated
OAc
(m/e)=556
OAc
-CH3COOH
+
.
OAc
Ph
N
Ph
Ph
N
O
Ph
H
N
C N
S
S
N
H
H
OAc
S
H2N
H
AcO
S
(m/e)=286
OAc
H
(m/e)=616
OAc
OAc
OH
OAc
H
O+
O+
O+
H
-2CH3COOH
H
OAc
AcO
OAC
OAc
H
(m/e)=169
CH2
(m/e)=211
(m/e)=331
OAc
OAc
H
O+
O+
O+
H
O
-CH3COOH
H3C
O
-CH2=C=O
-CH3COOH
H
H
O
O
(m/e)=109
(m/e)=169
OAc
(m/e)=271
Scheme-X: Schematic mechanism of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidone through mass
spectral fragments

Vol. 30, No. 10 (2018)
Synthesis of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines 2315
TABLE-2
fragmented peaks with their relative abundance are listed in
Table-2. The probable fragmentation pattern of molecular ion
is shown in Scheme-XI.
MASS SPECTRAL DATA OF ACETYLATED AND DE-
ACETYLATED GLUCOPYRANOSYLIMINO NUCLEOSIDES
S.
No.
Relative
abundance (%)
Ion
m/e
Conclusion
Acetylated glucopyranosylimino nucleoside
3-Phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-gluco-
pyranosylimino-1,2,4-ditiazolidine (i.e. acetylated glucopyra-
nosylimino nucleoside) have been synthesized from glucose.
De-acetylating of product have been carried out to give
4-phenyl-5-tetra-hydroxy-β-D-glucopyranosyl imino-1,2,4-
dithiazolidine and broadly called as de-acetylated glucopyra-
nosylimino nucleoside throughout the paper.
Both the acetylated and de-acetylated glucopyranosylimino
nucleoside have been structurally confirmed by spectral
analysis which includes UV, IR, NMR and mass spectroscopy.
Schematic fragmentation pattern of both acetylated and de-
acetylated glucopyranosylimino nucleoside have been studied.
1
2
3
4
5
6
7
8
9
M+
615
616
574
556
496
331
286
271
243
211
229
169
109
Not located
Protonated
(M-CH2=C=O)
100
3
17
1
65
5
14
0.02
4.5
7.5
33
6
(M-CH3COOH)
(M-CH3COOH CH2CO)+
(MC12H10N3S2)++ i.e. TAG
(M-C16H17O9)+
(TAG-3CH3COOH)+
(TAG-AcOCH=O)+
10 (TAG-2CH3COOH)
11 (TAG-CH3COOH, CH2=O)
12 (TAG-2CH3COOH, CH2=O)+
13 (TAG-3CH3COOH, CH2CO)+
De-acetylated glucopyranosylimino nucleoside
447
ACKNOWLEDGEMENTS
1
2
3
4
5
6
7
8
M+
7.4
10
45.4
16.7
42.3
57.5
M-C6H11O5
C13H10N2S
C6H12O6
C7H5NS2
C7H5NS
C6H5N
285
225
180
167
135
93
The authors acknowledge CDRI, Lucknow, India for spectral
analyses of samples. The authors acknowledge to Department
of Chemistry, RTM Nagpur University, Nagpur, India for provi-
ding the necessary research facilities.
CONFLICT OF INTEREST
C6H5
77
100
The authors declare that there is no conflict of interests
regarding the publication of this article.
The mass spectrum for de-acetylated glucopyranosyl
nucleoside shows the molecular ion peak as well as other
Ph
Ph
C6H12O6
HN C N
HS
(m/e)=225
Ph
(m/e)=180
Ph
N
C N
S
HN
C
S
S
Ph N
S
(m/e)=285
(m/e)=167
OH
H
Ph
N
Ph
N
O
H
S
N
H
H
S
OH
H
HO
OH
(m/e)=447
C6H5N
C6H5]+
(m/e)=77
(m/e)= 93
Scheme-XI: Schematic mechanism of 3-phenylimino-4-phenyl-5-tetra-hydroxy-β-D-glucopyranosylimino-1,2,4-dithiazolidone through mass
spectral fragments

2316 Hardas et al.
Asian J. Chem.
10. J.F.J. Dippy, S.R.C. Hughes andA. Rozanski, J. Chem. Soc., 2492 (1959);
https://doi.org/10.1039/jr9590002492.
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