8972
K.-C. Lu et al. / Tetrahedron 60 (2004) 8967–8973
4.1.4. Methyl (5-acetamido-9-thioacetyl-4,7,8-tri-O-
acetyl-3,5,9-trideoxy-b-D-glycero-D-galacto-2-nonulo-
pyranoside)onate (4e). 1H NMR (CDCl3, 400 MHz): d 1.89
(s, 3H), 2.02 (s, 3H), 2.04 (s, 3H), 2.16 (s, 3H), 2.20–2.25
(m, 2H), 2.31 (s, 3H), 2.72 (dd, 1H, JZ10.0, 14.4 Hz), 3.73
(dd, 1H, JZ2.8, 14.4 Hz), 3.84 (s, 3H), 4.13–4.20 (m, 1H),
4.22 (dd, 1H, JZ2.0, 10.0 Hz), 5.01 (ddd, 1H, JZ2.8, 4.4,
10.0 Hz), 5.19–5.26 (m, 1H)), 5.34 (dd, 1H, JZ2.0, 4.4 Hz),
5.82 (d, 1H, JZ10.0 Hz). 13C NMR (CDCl3, 100 MHz): d
20.89, 23.13, 29.47, 30.47, 49.73, 53.35, 68.78, 69.40,
71.09, 73.11, 94.94, 169.02, 170.33, 170.44, 170.76, 171.09,
195.94. HRMS (EI) Calcd for C20H30O12NS [MCH]C:
508.2489. Found: 508.1479.
National Science Council of Taiwan (NSC91-3112-P-001-
041-Y and 91-2113-M-001-013) for financial support.
References and notes
1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis, 3rd ed.; Wiley: New York, 1999;
pp 17–245. (b) Kocienski, P. J. Protecting Groups; Thieme:
New York, 1994; pp 21–94. (c) Larock, R. C. Comprehensive
Organic Transformations, 2nd ed.; VCH: New York, 1999;
pp 1955–1957.
4.1.5. 1,2,3,4-Diisopropylidene-6-acetyl-D-galactopyra-
nose (50). H NMR (CDCl3, 400 MHz): d 1.33 (s, 3H),
2. Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115,
3358–3359.
1
1.34 (s, 3H), 1.45 (s, 3H), 1.52 (s, 3H), 2.09 (s, 3H), 4.01–
4.04 (m, 1H), 4.19 (dd, 1H, JZ7.6, 11.6 Hz), 4.24 (dd, 1H,
JZ8.0, 2.0 Hz), 4.29 (dd, 1H, JZ4.8, 11.6 Hz), 4.25 (dd,
1H, JZ5.2, 2.4 Hz), 4.62 (dd, 1H, JZ2.4, 8.0 Hz), 5.54 (d,
1H, JZ5.2 Hz). 13C NMR (CDCl3, 125 MHz): d 20.71,
24.36, 24.82, 24.83, 25.83, 25.85, 63.36, 63.84, 70.32,
70.58, 70.95, 96.17, 108.61, 109.46, 170.79. HRMS (FAB)
Calcd for C14H23O7 [MCH]C: 303.1439. Found: 303.1444.
3. (a) Verkade, J. G.; Ilankumaran, P. J. Org. Chem. 1999, 64,
9063–9066. (b) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver,
S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, J. M.
J. Org. Chem. 1993, 58, 7286–7288.
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1896–1897. (b) Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001,
10, 1584–1586. (c) Pansare, S. V.; Malusare, M. G.; Rai,
A. N. Synth. Commun. 2000, 30, 2587–2592. (d) Orita, A.;
Nagano, Y.; Nakazawa, K.; Otera, J. Synlett 2000,
599–602. (e) Sabitha, G.; Reddy, B. V. S.; Srividya, R.;
Yadav, J. S. Synth. Commun. 1999, 29, 2311–2315. (f)
Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett
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J. Synlett 1999, 1927–1929. (h) Chandrasekhar, S.;
Ramachander, T.; Takhi, M. Tetrahedron Lett. 1998, 39,
3263–3266. (i) Damen, E. W. P.; Braamer, L.; Scheeren,
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E.; Daugulis, O. J. Org. Chem. 1996, 61, 5702–5703. (k)
Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H.
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4.1.6. 2,3,5-O-Acetyl-N-acetyl-cytidine (52). 1H NMR
(CDCl3, 400 MHz): d 2.05 (s, 3H), 2.05–2.07 (m, 1H),
2.07 (s, 3H), 2.11 (s, 3H), 2.24 (s, 3H), 4.36–4.39 (m, 3H),
5.30 (t, 1H, JZ5.6 Hz), 5.44 (dd, 1H, JZ3.6, 5.6 Hz), 6.01
(d, 1H, JZ3.6 Hz), 7.47 (d, 1H, JZ7.6 Hz), 7.91 (d, 1H,
JZ7.6 Hz). 13C NMR (CDCl3, 125 MHz): d 20.54, 20.89,
24.95, 40.85, 62.72, 69.65, 73.84, 79.87, 89.64, 97.37,
144.24, 155.02, 163.33, 169.56, 169.64, 170.33, 131.37.
HRMS (FAB) Calcd for C17H22O9N3 [MCH]C: 412.1350.
Found: 412.1356.
4.1.7. O-Acetyl-N-carbo-tert-butyloxy-serine-tert-butyl-
ester (53). H NMR (CDCl3, 400 MHz): d 1.46 (s, 9H),
¨
¨
5. Hofle, G.; Steglich, W.; Voruggen, H. Angew. Chem., Int. Ed.
Engl. 1978, 17, 569–583.
1
1.46 (s, 9H), 2.05 (s, 3H), 4.28 (dd, 1H, JZ4.4, 12.0 Hz),
4.44–4.46 (m, 2H), 5.29 (d, 1H, JZ7.2 Hz). 13C NMR
(CDCl3, 100 MHz): d 20.62, 27.90, 28.28, 53.42, 64.73,
80.07, 82.70, 155.19, 168.70, 170.45. HRMS (FAB) Calcd
for C14H26O6N [MCH]C: 304.1760. Found: 304.1755.
6. Vogel, A. I. Vogel’s Textbook of Practical Organic Chemistry,
5th ed.; Wiley: New York, 1989; pp 644–651.
7. Dasguta, F.; Singh, P. P.; Srivastava, H. C. Carbohydr. Res.
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8. Chen, C.-T.; Kuo, J.-H.; Li, C.-H.; Barhate, N. B.; Hon, S.-W.;
Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.;
Lin, J.-S.; Liu, C.-J.; Chou, Y-C. Org. Lett. 2001, 3,
3729–3732.
4.1.8. 2-(9H-Fluoren-9-ylmeyhoxycarbonylamino)-3-
acetyl-butyric acid allyl ester (54). 1H NMR (CDCl3,
400 MHz): d 1.31 (d, 3H, JZ6.4 Hz), 2.04 (s, 3H), 4.27 (t,
1H, JZ6.8 Hz), 4.47 (d, 2H, JZ6.8 Hz), 4.54 (dd, 1H, JZ
2.6, 9.8 Hz), 4.60–4.70 (m, 2H), 5.28 (dd, 1H, JZ1.2,
10.4 Hz), 5.35 (dd, 1H, JZ1.2, 16.6 Hz), 5.45–5.52 (m,
2H), 5.86–5.95 (m, 1H), 7.30–7.35 (m, 2H), 7.40–7.44 (m,
2H), 7.62–7.65 (m, 2H), 7.79 (d, 2H, JZ7.6 Hz). 13C NMR
(CDCl3, 125 MHz): d 17.06, 21.03, 40.97, 42.74, 47.28,
57.78, 66.51, 67.40, 70.48, 119.36, 120.13, 120.14, 125.19,
127.23, 127.89, 129.62, 131.44, 141.44, 143.76, 143.95,
156.66, 169.73, 169.84. HRMS (FAB) Calcd for
C24H26O6N [MCH]C: 424.1766. Found: 424.1760.
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851–855.
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MacFarlane, D. R.; Thomson, R. J.; von Itzstein, M. Chem.
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Acknowledgements
16. Although the decomposition of LiClO4 starts at ca 400 8C, a
violent explosion by using LiClO4 in Et2O under reflux has
been reported: Silva, R. A. Chem. Eng. News 1992.
The authors would like to thank Academia Sinica
(AS92IC6), National Taiwan Normal University, and