H-6a and H-6b), 3.71 (1H, t, J5,6 8.4 Hz, H-5), 2.10, 2.07, 2.02
and 1.95 (12H, 4 s, 4xCOCH ); d (75.47 MHz; CDCl ) 170.6,
Acknowledgements
3
C
3
Premanand R. Patil thanks NIPER for the research fellowship
and Ravindranathan Kartha thanks the Department of Science
and Technology, New Delhi for financial assistance.
1
33.0, 129.4, 128.7, 87.1, 74.9, 72.5, 67.7, 62.1, 21.4 and 21.1;
+
MALDI-TOF MS C20
H
24
O
9
S [M] calcd. m/z 440.464, found
+
+
4
79.590 (M + K , 59%), 463.586 (M + Na , 73%), 331.515
+
(
M-SPh , 100%).
References
4
-Methyl-phenyl 2,3,4,6-tetra-O-acetyl-1-thio-a-D-
1
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(
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H-2 and H-4), 4.57 (1H, ddd, H-5), 4.28 (1H, dd, J5,6a 5.1 Hz and
6a,6b 12.3 Hz H-6a), 4.05 (1H, dd, J5,6b 2.7 Hz and J6a,6b 12.3 Hz
3
); vmax (KBr)/cm 2945.3, 1752.8, 1374.8, 1224.4,
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H-6b), 2.32 (3H, 1 s, CH
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) 2.10, 2.08, 2.05 and 2.03 (12H, 4 s,
(75.47 MHz; CDCl ) 170.5, 169.9, 169.8, 169.6,
38.1, 132.5, 129.9, 128.6, 85.4, 70.8, 70.4, 68.6, 68.0, 62.0, 20.1,
4
1
2
4
1
xCOCH
3
); d
C
3
4 (a) G. Chitra, K. K. Bhutani, I. P. Singh, and K. P. R. Kartha,
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+
0.7 and 20.6; MALDI-TOF MS C21
H
26
9
O S [M] calcd. m/z
+
+
54.491, found 493.156 (M + K , 34%), 477.157 (M + Na ,
00%), 331.085 (M-SPh-4-CH
+
3
, 54%).
2
006, 25, 303–313and the references cited therein.
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6
(a) J. Bogusiak and W. Szeja, Pol. J. Chem., 1985, 59, 293–298; J.
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were allowed to mix in a SS jar (capacity, 50 mL) containing
1
This led to the complete conversion of the glycosyl bromide to
the corresponding glycosyl isothiourea derivative (21/22, TLC:
0 SS balls (10 mm o.d.) for 2 h at 400 rpm in the ball mill.
2
006, 16, 1668–1672.
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3
N (10 mol equiv) was
7
then added to the jar and was milled for 30 min followed
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2
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2
,4-dinitrophenol/1, 1.5 mmol) and mixing was continued
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(
1
c) A. Bruckmann, A. Krebs and C. Bolm, Green Chem., 2008, 10,
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(
preferred as a greener alternative, is equally effective) followed
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3
40, 1393–1396; (b) N. Khiar and M. Martin-Lomas, J. Org. Chem.,
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1
separatedandwas washed successivelywith aq. Na
10%, w/v) and water, dried (Na SO ), and was concentrated
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2
CO solution
3
9
(a) C.-S. Chao, M.-C. Chen, S.-C. Lin and K.-K. T. Mong, Carbohydr.
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(
2
4
2
10b
10 (a) S.-S. Weng, Y.-D. Lin and C.-T. Chen, Org. Lett., 2006, 8, 5633–
title product (23 /24 after purification by column chromato-
5
636; (b) B. Mukhopadhyay, K. P. R. Kartha, D. A. Russell and R. A.
17
13
graphy and 25 /26 by recrystallization from Et O–n-Hex).
2
Field, J. Org. Chem., 2004, 69, 7758–7760.
The spectral data were in accordance with the expected structure
and in agreement with literature values.
11 H. Ando, H. Ishida and M. Kiso, in Best Synthetic Methods:
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1
2 M. A. Oturan, M. M e´ debille, S. A. Patil and R. S. Klein,
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1
3 T. Fujihira, T. Takido and M. Seno, J. Mol. Catal. A: Chem., 1999,
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37, 65–75.
1
1
4 R. J. Pearson, Ph.D. Thesis, University of St. Andrews, UK, 2001.
5 W. A. Bonner and J. E. Kahn, J. Am. Chem. Soc., 1951, 73, 2241–
The glycosyl halide (8, 1 mmol) and KSAc (2.5 mmol) were
allowed to mix in a SS jar (capacity, 50 mL) containing 10 SS
balls (10 mm o.d.) for 2 h at 400 rpm in the ball mill. The reaction
was found to be complete at this time (TLC: eluent, EtOAc–n-
Hex = 1 : 1). Then, DCM or EtOAc (20 mL) was added and the
mixture was washed in a separating funnel with water and was
2
245.
16 K. P. R. Kartha and R. A. Field, J. Carbohydr. Chem., 1998, 17,
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1
1
7 H. Driguez and W. Szeja, Synthesis, 1994, 1413–1414.
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18
dried to afford the thioacetate as crystals (27, 98%).
9
56 | Green Chem., 2009, 11, 953–956
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