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Der Pharma Chemica, 2011, 3 (6):28-31

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ISSN 0975-413X
CODEN (USA): PCHHAX

Synthesis of Some Novel 2-S-tetra-O-benzoyl-D-glucopyranosyl-1-

aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-isothiobiurets
Kedar P. Pande1 and Shirish P. Deshmukh2*
1
Mauli Group of Institution’s, College of Engineering and Technology, Shegaon (M.S.) India
2
P. G. Department of Chemistry, Shri Shivaji College, Akola (M.S.) India
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ABSTRACT

The study of S-and N-glycosides is important in carbohydrate chemistry. Sugar isocyanate is

good precursors and versatile intermediate for synthesis of S- and N-glycosides. Carbohydrates
play an important role in the number of biological events and play an important role in their
synthetic strategy as well. Similarly the amino sugars are an important class of glycosidase
inhibitors and are arousing great interest as potential therapeutic agents. Several 2-S-tetra-O-
benzoyl-D-glucopyranosyl-1-aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-isothiobiurets have been
synthesized for the first time by the interaction of hepta-O-benzoyl-β-D-lactosyl isocyanate and
S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl isothiocarbamides. All the synthesized compounds
were characterized on the basis of elemental analysis and IR, 1HNMR and Mass spectral
analysis. The polarimetric study of the compounds was carried out.

Key words: Lactosyl isocyanate, glucopyranosyl isothiocarbamides, lactosyl isothiobiurets.

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INTRODUCTION

Glycosyl amines, glycosyl guanidine derivatives, glycosyl thiocarbamides have several

medicinal applications such as antitumor agent1, antilukemic agent2, antibacterial properties3,
antimetastatic compounds4 and in many other ways5. S-and N-glycosylated derivatives and their
utilities in medicinal chemistry have been extensively studied6-19. The synthesis and
pharmacological evaluation of the varieties of glycosyl isothiobiurets and isodithiobiurets have
been reported.

In present communication we report the synthesis of 2-S-tetra-O-benzoyl-D-glucopyranosyl-1-

aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-isothiobiurets (III) by the interaction of hepta-O-
benzoyl-β-D-lactosyl isocyanate (I) and various S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl
isothiocarbamides (II).

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MATERIALS AND METHODS

Optical rotations [α]D31 were measured on the Equip-Tronics EQ-800 Digital Polarimeter at 310C
in CHCl3. IR Spectra were recorded on Perkin-Elmer spectrum RXI FTIR Spectrometer. 1H
NMR was obtained on Bruker DRX-300 NMR Spectrometer. Samples were prepared in CDCl3
with TMS as an internal reference. The mass spectra were obtained on Thermo Fennigan LCQ
Advantage max ion trap mass spectrometer.

General Procedure:-
2-S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-isothiobiurets (IIIa-
g) (Scheme 1)
A 0.005M of S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl isothiocarbamides (IIa-g) in a 5ml of
benzene was added to a 0.005M solution of hepta-O-benzoyl-β-D-lactosyl isocyanate (I) in 15ml
benzene the reaction mixture was reflux over boiling water bath for 5hr. After refluxing, the
solvent was distilled off and the sticky residue obtained was triturated with petroleum ether (60-
80 0C) to afford a solid (IIIa-g). The product was purified by chloroform petroleum ether. The
product was checked by TLC. The percent yield, M.P., Optical rotation, elemental analysis
shown in Table 1.
IIIa: IR (KBr):- ν 3068 (Ar-H), 1729 (C=O), 3465 (N-H), 1653 (C=N), 1269 (C-N), 771(C-S),
1101 & 1027 cm-1 (Characteristic of Lactose); 1H NMR (CDCl3):- δ 8.02-7.11 (42H, Ar-H), δ
6.28-3.89 (14H, lactosyl and glucosyl protons); Mass: - m/z 1825 (M+), 1053, 948,932, 579,
531, 135. Anal. Calcd. for C103H83O27N3SCl, Requires: C, 67.72; H, 4.54; N, 2.30; S, 1.75;
Found: C, 67.68; H, 4.50; N, 3.24; S, 1.71%.

Table 1:- Characterization data of 2-S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl-5-hepta-O-benzoyl-β-D-

lactosyl-2-isothiobiurets (IIIa-g).
Reactants: -
1) Hepta-O-benzoyl-β-D-lactosyl isocyanate (I) [0.005M].
2) S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl isothiocarbamides (IIa-g) [0.005M].

Analysis
o 31 Found
Sr. No. Compd. %Yield m. p. ( C) [α]D (CHCl3)
(Required)
N S
+50.01 o 1.71
1. IIIa 60.10 130-132 2.30 (3.24)
(c, 0.930) (1.75)
+66.4o 2.21 1.70
2. IIIb 49.45 118
(c, 0.930) (2.28) (1.74)
+82.9o 2.22 1.71
3. IIIc 53.26 110
(c, 0.930) (2.28) (1.74)
+42.32o 2.23 1.72
4. IIId 54.34 122
(c, 0.930) (2.28) (1.74)
+52.14o 2.21 1.67
5. IIIe 69.89 112
(c, 0.930) (2.25) (1.72)
+69.28o 2.19 1.68
6. IIIf 53.76 127
(c, 0.930) (2.25) (1.72)
+ 35.59o 2.22 1.69
7. IIIg 44.08 108
(c, 0.930) (2.25) (1.72)

IIIc: IR (KBr):- ν 3066 (Ar-H), 1730 (C=O), 3451 (N-H), 1653 (C=N), 1270 (C-N), 709 (C-S),
1069 & 1025 cm-1 (Characteristic of Lactose); 1H NMR (CDCl3):- δ 8.20-7.12 (44H, Ar-H),δ
6.22-3.73 (14H, lactosyl and glucosyl protons); Mass: - m/z 1839 (M+), 1053, 948,932, 579, 531,
135. Anal. Calcd. for C104H85O27N3SCl, Requires: C, 67.86; H, 4.62; N, 2.28; S, 1.74; Found: C,
67.79; H, 4.59; N, 2.22; S, 1.71%.
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IIIf: IR (KBr):- ν 3067 (Ar-H), 1729 (C=O), 3448 (N-H), 1601 (C=N), 1270 (C-N), 772 (C-S),
1099 & 1025 cm-1 (Characteristic of Lactose); 1H NMR (CDCl3):- δ 8.28-7.19 (44H, Ar-H),δ
5.88-4.19 (14H, lactosyl and glucosyl protons); Mass: - m/z 1859 (M+), 1053, 948,932, 579, 531,
135. Anal. Calcd. for C103H82O27N3SCl, Requires: C, 66.46; H, 4.40; N, 2.25; S, 1.72; Found: C,
66.40; H, 4.32; N, 2.19; S, 1.68%.

RESULTS AND DISCUSSION

2-S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl-5-hepta-O-benzoyl-β-D-lactosyl-2-isothiobiurets
(IIIa-g) (Scheme 1) were prepared by the interaction of hepta-O-benzoyl-β-D-lactosyl
isocyanate (I) and various S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl isothiocarbamides (IIa-g)
in benzene medium for 5 hr. After condensation, solvent was distilled off and sticky residue
obtained which was triturated with petroleum ether (60-80 0C) to afford product. It was purified
by chloroform-Petroleum ether.

Scheme 1

BzO
OBz OBz O
OBz
OBz
O O
O OBz
BzO N=C=O + RNH OBz
BzO
OBz OBz
(I) HN C S (II)
β-D-lactosyl isocyanate
Hepta-O-benzoyl-β S-tetra-O-benzoyl-β β-D-glucosyl-
1-aryl isothoicarbamides

Benzene
Reflux, 5hr
BzO
O
OBz
OBz OBz OBz
O RNH OBz
O OBz
O NH C N C S
BzO BzO
OBz OBz O

(III)
β-D-glucosyl-1-aryl-5-hepta-O-benzyl-β
2-S-tetra-O-benzoyl-β β-D-lactosyl-2-isothiobiurets
Where, Bz- COC6H5
R = a) phenyl, b) o-tolyl, c) m-tolyl, d) p-tolyl,
e) o-Cl-phenyl, f) m-Cl-phenyl, g) p-Cl-phenyl.

Acknowledgement
Authors are thankful to SAIF, C.D.R.I. Lucknow for providing spectral data, Dr. S.G. Bhadange,
Principal of Shri Shivaji College, Akola and Dr. C.M. Jadhao, Principal, Mauli Group of
Institution’s, College of Engg. and Technology, Shegaon for providing necessary facilities.

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