A. T. Khan, M. M. Khan / Carbohydrate Research 345 (2010) 2139–2145
2145
3
.25.
D
-Galactose dipropyl dithioacetal (12b)
Acknowledgments
White needles: mp 151–154 °C (recrystallized from 3:1:1 H
2
O–
MMK is thankful to UGC, New Delhi, India for his senior re-
search fellowship. The authors are grateful to the Director, IIT
Guwahati, for providing the general facilities to carry out this work.
2
5
EtOH–EtOAc); ½
a
ꢀ
+10.8 (c 1.0, MeOH).
D
3
.26. 2,3,4,5,6-Penta-O-acetyl-
D-galactose dipropyl dithioacetal
(
12c)
Supplementary data
2
D
5
Syrup: ½aꢀ
+6.6 (c 0.80, MeOH); IR (KBr):
H NMR (400 MHz; CDCl ): d 5.79 (dd, 1H, J = 9.6,
.0 Hz, H-3), 5.24 (d, 1H, J = 9.6, 2.0 Hz, H-4), 5.20–5.17 (m, 1H,
m 1750, 1371,
Complete crystallographic data of 1c and 3c for the structural
analyses have been deposited with the Cambridge Crystallographic
Data Centre. The CCDC Nos. are 687605 and 687604, respectively,
for 1c and 3c. Copies of this information may be obtained free of
charge from the Director, Cambridge Crystallographic Data Centre,
ꢁ
1
1
1
2
215 cm
;
3
H-5), 5.15 (dd, 1H, J = 8.4, 2.0 Hz, H-2), 4.28 (dd, 1H, J = 12.0,
5
0
.2 Hz, H-6), 3.84 (dd, 1H, J = 12.0, 7.2 Hz, H-6 ), 3.79 (d, 1H,
J = 8.4 Hz, H-1), 2.70–2.60 (m, 4H, 2 ꢂ SCH
2
CH
), 2.10 (s, 3H, COCH
), 1.64–1.52 (m, 4H, 2 ꢂ SCH CH ), 0.99 (t, 3H, J = 7.6 Hz,
CH ), 0.98 (t, 3H, J = 7.2 Hz, SCH
100 MHz; CDCl ): d 170.7, 170.6, 170.4, 170.1, 169.7, 70.7, 68.5,
8.2, 68.0, 62.4, 52.7, 33.6, 33.1, 22.7, 22.6, 21.2, 21.0, 20.9, 13.8,
3.7. Anal. Calcd for C22 (524.65): C, 50.37; H, 6.92; S,
2.22. Found: C, 50.26; H, 6.85; S, 12.13.
2
), 2.13 (s, 3H,
1
COCH
COCH
SCH
3
), 2.11 (s, 6H, 2 ꢂ COCH
3
3
), 2.02 (s, 3H,
1
13
3
2
2
1
3
2
CH
2
3
2
CH
2
CH
3
);
C NMR
(
3
6
1
1
36 10 2
H O S
References
1
2
3
4
.
.
.
.
Fischer, E. Ber. Dtsch. Chem. Ges. 1894, 27, 673–679.
Eitelman, S. J.; Horton, D. Carbohydr. Res. 2006, 341, 2658–2668.
Armstrong, R. W.; Teegarden, B. R. J. Org. Chem. 1992, 57, 915–922.
Khan, A. T.; Ahmed, W.; Schmidt, R. R. Carbohydr. Res. 1996, 280, 277–286.
3
.27.
D-Mannose dipropyl dithioacetal (13b)
White reddish needles: mp 130–132 °C (recrystallized from
5. Bos, J. C.; Vloon, W. J.; Koomen, G. J.; Pandit, U. K. Tetrahedron 1991, 47, 6787–
794.
25
6
3
:1:1 H
2
O–EtOH–EtOAc); ½
a
ꢀ
+4.3 (c 1.0, MeOH).
D
6
7
.
.
White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224–6233.
Pattenden, G.; González, M. A.; Little, P. B.; Millan, D. S.; Plowright, A. T.;
Tornos, J. A.; Ye, T. Org. Biomol. Chem. 2003, 1, 4173–4208.
3
.28. 2,3,4,5,6-Penta-O-acetyl-D-mannose dipropyl dithioacetal
8
.
.
Tadano, K.; Maeda, H.; Hoshino, M.; Iimura, Y.; Suami, T. J. Org. Chem. 1987, 52,
(
13c)
1946–1956.
9
Timmer, S. M. S.; Stocker, B. L.; Seeberger, P. H. J. Org. Chem. 2006, 71, 8294–
8297.
2
5
Syrup: ½aꢀ
+26.1 (c 1.2, MeOH); IR (KBr):
H NMR (400 MHz; CDCl ): d 5.74 (dd, 1H, J = 7.2,
.6 Hz, H-3), 5.50 (dd, 1H, J = 9.2, 1.6 Hz, H-4), 5.28 (dd, 1H,
m
1750, 1372,
D
ꢁ1
1
1
1
218 cm
;
3
10. Kim, J. Y.; Namshin, J. E.; Chun, K. H. Bull. Korean Chem. Soc. 1996, 17, 478–480.
11. McAuliffe, J. C.; Hindsgaul, O. J. Org. Chem. 1997, 62, 1234–1239.
12. Wolfrom, M. L.; Thompson, A. Methods Carbohydr. Chem. 1963, 2, 427–430.
13. Zinner, H. Chem. Ber. 1950, 83, 275–277.
J = 7.2, 6.0 Hz, H-2), 5.09–5.05 (m, 1H, H-5), 4.20 (dd, 1H, J = 12.8,
2
0
.4 Hz, H-6), 4.08 (dd, 1H, J = 12.8, 5.2 Hz, H-6 ), 3.87 (d, 1H,
14. Wolfrom, M. L. J. Am. Chem. Soc. 1930, 52, 2464–2474.
1
1
5. Funabashi, M.; Arai, S.; Shinohara, M. J. Carbohydr. Chem. 1999, 18, 333–341.
6. Chang, Y.-K.; Lee, B-. Y.; Kim, D. J.; Lee, G. S.; Jeon, H. B.; Kim, K. S. J. Org. Chem.
J = 6.0 Hz, H-1), 2.72–2.64 (m, 2H, SCH
SCH CH ), 2.10 (s, 3H, COCH ), 2.08 (s, 3H, COCH
ꢂ COCH ), 2.05 (s, 3H, COCH ), 1.66–1.54 (m, 4H, 2 ꢂ SCH
.01 (t, 3H, J = 7.6, SCH CH CH ), 0.98 (t, 3H, J = 7.6 Hz,
CH CH ): d 170.8, 170.1, 169.9,
); 13C NMR (100 MHz; CDCl
1.4, 69.2, 68.2, 67.4, 62.0, 52.1, 33.5, 33.2, 22.6, 22.5, 21.0, 20.9,
3.7. Anal. Calcd for C22 (524.65): C, 50.37; H, 6.92; S,
2.22. Found: C, 50.29; H, 6.80; S, 11.97.
2
CH
2
), 2.62–2.53 (m, 2H,
), 2.07 (s, 6H,
CH ),
2
2
3
3
2
005, 70, 3299–3302.
17. Zinner, H.; Schneider, U. Chem. Ber. 1963, 96, 2159–2164.
2
1
SCH
7
1
1
3
3
2
2
1
8. Khan, A. T.; Ali, M. A.; Goswami, P.; Choudhury, L. H. J. Org. Chem. 2006, 71,
961–8963.
9. Khan, A. T.; Sahu, P. R.; Majee, A. J. Mol. Catal. A: Chem. 2005, 226, 207–212.
2
2
3
8
2
2
3
3
1
20. Khan, A. T.; Mondal, E.; Ghosh, S.; Islam, S. Eur. J. Org. Chem. 2004, 2002–2009.
21. Khan, A. T.; Parvin, T.; Choudhury, L. H. J. Org. Chem. 2008, 73, 8398–8402. and
36 10 2
H O S
references cited therein.
2
2
2
2. Jiang, B.; Dou, Y.; Xu, X.; Xu, M. Org. Lett. 2008, 10, 593–596.
3. Bhalerao, D. S.; Akamanchi, K. G. Synlett 2007, 2952–2956.
4. Das, B.; Srinivas, Y.; Holla, H.; Laxminarayana, K.; Narender, R. Tetrahedron Lett.
3
.29. 2,3,4,6-Tetra-O-benzyl-
D-glucose diethyl dithioacetal (14b)
2007, 48, 6681–6683.
2
5. Xiong, D.-C.; Zhang, L.-H.; Ye, X.-S. Adv. Synth. Catal. 2008, 350, 1696–1700.
2
D
5
+27 (c 1.0, MeOH), lit.16
25
White syrup: ½
a
ꢀ
½
a
ꢀ
+20.0 (c 0.97,
D
m 3492, 1454,
26. Khan, A. T.; Parvin, T.; Choudhury, L. H. Tetrahedron 2009, 65, 9513–9526.
27. Khan, A. T.; Khan, M. M. Carbohydr. Res. 2010, 345, 154–159.
28. Misra, A. K.; Tiwari, P.; Madhusudan, S. K. Carbohydr. Res. 2005, 340, 325–329.
3
7
25
D
CHCl
1
3
), lit.
½
a
ꢀ
+19.5 (c 2.3, CHCl
3
); IR (KBr):
): d 7.38–7.23 (m, 20H,
ArH), 4.89 (d, 1H, J = 11.2 Hz, CHH), 4.80 (d, 1H, J = 11.2, CHH),
100 cm ; 1H NMR (400 MHz; CDCl
ꢁ1
3
2
9. Kameda, Y.; Asano, N.; Yoshikawa, M.; Matsui, K. J. Antibiot. 1982, 35, 1624–
626.
30. Furukawa, N.; Inoue, T.; Aida, T.; Oae, S. J. Chem. Soc., Chem. Commun. 1973, 212.
1
4
4
1
.79 (d, 1H, J = 11.6, CHH), 4.67 (d, 1H, J = 11.6 Hz, CHH), 4.59–
.49 (m, 4H, 2 ꢂ CH ), 4.27 (dd, 1H, J = 6.8, 3.6 Hz, H-3), 4.14 (dd,
H, J = 6.8, 4.0 Hz, H-2), 4.15–4.03 (m, 1H, H-5), 3.93 (d, 1H,
3
1. Sato, K.; Akai, S.; Youda, H.; Kojima, M.; Sakuma, M.; Inaba, S.; Kurosawa, K.
Tetrahedron Lett. 2005, 46, 237–243.
2. Horton, D. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel
Dekker: New York, 1997; pp 35–52.
2
3
J = 4.0 Hz, H-1), 3.71 (dd, 1H, J = 6.8, 3.6 Hz, H-4), 3.66 (dd, 1H,
J = 10.0, 4.0 Hz, H-6), 3.61 (dd, 1H, J = 10.0, 5.6 Hz, H-6 ), 3.08 (d,
H, J = 5.2 Hz, OH), 2.66 (q, 2H, J = 7.6 Hz, SCH
), 1.18 (t, 3H, J = 7.2 Hz, SCH
); C NMR (100 MHz; CDCl
38.1, 128.6, 128.4, 128.3, 128.2, 128.03, 128.0, 127.96, 127.9,
27.6, 82.9, 80.3, 77.5, 75.5, 75.1, 73.7, 73.0, 71.6, 71.1, 54.0,
0
33. Roberts, J. C.; Nagasawa, H. T.; Zera, R. T.; Fricke, R. F.; Goon, D. J. W. J. Med.
Chem. 1987, 30, 1891–1896.
3
35. Zissis, E.; Richtmyer, N. K. J. Am. Chem. Soc. 1952, 73, 4373–4377.
36. Zinner, H.; Wessely, K.; Bock, W.; Rieckhoff, K.; Strandt, F.; Nimmich, W. Chem.
Ber. 1957, 90, 500–515.
1
(
2
CH
CH ), 1.17 (t, 3H,
): d 138.7, 138.4,
3
), 2.60–2.50
4. Mahidhar, Y. V.; Rejesh, M.; Chaudhuri, A. J. Med. Chem. 2004, 47, 3938–3948.
m, 2H, SCH
2
CH
3
2
3
13
J = 7.6 Hz, SCH
2
CH
3
3
1
1
2
7
3
7. Gent, P. A.; Gigg, R. J. Chem. Soc., Perkin Trans. 1 1974, 1446–1455.
5.7, 25.5, 14.6. Anal. Calcd for C38
.17; S, 9.91. Found: C, 70.46; H, 7.03; S, 9.82.
36 5 2
H O S (646.28); C, 70.55; H,