Y. Yang et al. / Tetrahedron Letters 51 (2010) 1504–1507
1507
3. (a) Yu, B.; Sun, J. Chem. Asian J. 2009, 4, 642–654; (b) Yu, B.; Zhang, Y.; Tang, P. Eur.
J. Org. Chem. 2007, 5145–5161; (c) Pellissier, H. Tetrahedron 2004, 60, 5123–5162.
4. (a) Bliard, C.; Massiot, G.; Nazabadioko, S. Tetrahedron Lett. 1994, 35, 6107–6108;
(b) Peng, W.; Sun, J.; Lin, F.; Han, X.; Yu, B. Synlett 2004, 259–262; (c) Peng, W.;
Han, X.; Yu, B. Synthesis 2004, 1641–1647; (d) Wang, P.; Li, C.; Zang, J.; Song, N.;
Zhang, X.; Li, Y. Carbohydr. Res. 2005, 340, 2086–2096; (e) Zhu, C.; Tang, P.; Yu, B.
J. Am. Chem. Soc. 2008, 130, 5872–5873; (f) Zhu, S.; Li, Y.; Yu, B. J. Org. Chem.
2008, 73, 4978–4985; (g) Gauthier, C.; Legault, J.; Rondeau, S.; Pichette, A.
Tetrahedron Lett. 2009, 50, 988–991; (h) Gauthier, C.; Legault, J.; Lavoie, S.;
Rondeau, S.; Tremblay, S.; Pichette, A. J. Nat. Prod. 2009, 72, 72–81; (i)
Krishnamurty, H. G.; Dabholkar, K.; Maheshwari, N. Synth. Commun. 1987, 17,
1323–1329; (j) Schneider, G.; Sembdner, G.; Schreiber, K.; Phirney, B. O.
Tetrahedron 1989, 45, 1355–1364; (k) Wen, X.; Sun, H.; Liu, J.; Cheng, K.; Zhang,
P.; Zhang, L.; Hao, J.; Zhang, L.; Ni, P.; Zographos, S. E.; Leonidas, D. D.; Alexacou,
K. M.; Gimisis, T.; Hayes, J. M.; Oikonomakos, N. G. J. Med. Chem. 2008, 51, 3540–
3554.
5. (a) Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604–3608; (b) Li, Y.; Yang,
X.; Liu, Y.; Zhu, C.; Yang, Y.; Yu, B. Chem. Eur. J. 2010. doi:10.1002/
chem.200902548. (A selective ester glycoside formation of oleanolic acid with
an arabinose ortho-hexynylbenzoate has been applied in the synthesis of a cyclic
triterpene saponin.); (c) Yang, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2009, 131, 12076–
12077.
6. For a comprehensive review on sugar 1,2-orthoesters, see: Kong, F. Carbohydr.
Res. 2007, 342, 345–373.
7. All the new compounds that appeared in this work give satisfactory analytical
45.7, 41.5, 40.9, 38.9, 38.6, 38.3, 36.8, 33.6, 32.9, 31.8, 30.5, 29.6, 28.1, 27.7, 27.1,
25.5, 23.4, 23.3, 22.6, 18.2, 16.5, 15.6, 15.2; HRMS (MALDI) m/z calcd for
C64H74O12Na [M+Na]+ 1057.5071, found 1057.5073. Compound 4: ½a 2D7
ꢂ
+23.3 (c
4.8, CHCl3); 1H NMR (400 MHz, CDCl3) d 7.92 (m, 8H), 7.47 (m, 12H), 6.04 (d,
J = 5.2 Hz, 1H), 5.72 (m, 1H), 5.40 (d, J = 8.8 Hz, 1H), 5.22 (t, J = 3.6 Hz, 1H), 4.76
(t, J = 4.0 Hz, 1H), 4.44 (dd, J = 3.6, 12.0 Hz, 1H), 4.29 (dd, J = 5.2, 11.6 Hz, 1H),
3.97 (m, 1H), 3.12 (m, 1H), 2.77 (dd, J = 4.4, 13.6 Hz, 1H), 1.07, 0.90, 0.88, 0.85,
0.82, 0.73, 0.68 (s, each 3H); 13C NMR (100 MHz, CDCl3) d 184.7, 166.2, 165.4,
164.8, 143.8, 137.9, 133.9, 133.7, 133.2, 130.3, 130.2, 130.0, 129.4, 129.3, 128.8,
128.6, 128.5, 128.2, 126.5, 122.8, 122.6, 97.7, 81.7, 72.9, 69.6, 68.7, 68.0, 64.3,
60.7, 55.8, 47.8, 46.7, 46.1, 41.7, 41.0, 39.4, 38.8, 38.7, 37.0, 34.0, 33.3, 32.7, 32.6,
30.9, 30.0, 28.5, 27.9, 26.2, 25.1, 23.8, 23.6, 23.1, 18.6, 17.4, 16.8, 15.5, 14.5;
HRMS (MALDI) m/z calcd for C64H74O12Na [M+Na]+ 1057.5080, found 1057.5073.
Compound 18: ½a 2D4
ꢂ
ꢃ44.4 (c 1.1, CHCl3); 1H NMR (300 MHz, CDCl3) d 6.01 (s,
1H), 5.23 (m, 2H), 5.12 (t, J = 9.9 Hz, 1H), 3.93 (m, 1H), 3.60 (dd, J = 11.1, 22.5 Hz,
2H), 2.16 (s, 3H), 2.06 (s, 3H), 1.99 (s, 3H), 1.24 (m, 9H); 13C NMR (100 MHz,
CDCl3) d 174.6, 170.2, 169.7, 90.9, 70.1, 69.5, 69.1, 68.9, 68.3, 44.8, 21.8, 20.7,
20.6, 20.5, 17.4; HRMS (MALDI) m/z calcd for C17H26O10Na [M+Na]+ 413.1416,
found 413.1418. Compound 19: ½a D24
ꢂ
+10.0 (c 1.1, CHCl3); 1H NMR (300 MHz,
CDCl3) d 5.41 (br s, 1H), 5.10 (dd, J = 3.3, 9.9 Hz, 1H), 5.02 (t, J = 9.9 Hz, 1H), 4.57
(br s, 1H), 3.50 (m, 3H), 2.10 (s, 3H), 2.05 (s, 3H), 1.70 (s, 3H), 1.20 (d, J = 6.3 Hz,
3H), 1.12 (s, 6H); 13C NMR (100 MHz, CDCl3) d 169.8, 169.7, 123.7, 97.1, 76.2,
70.5, 70.4, 69.1, 42.8, 24.0, 22.5, 22.3, 20.9, 20.7, 17.5; HRMS (MALDI) m/z calcd
for C17H26O10Na [M+Na]+ 413.1415, found 413.1418. Compound 20: ½a 2D4
ꢃ26.6
ꢂ
(c 0.4, CHCl3); 1H NMR (300 MHz, CDCl3) d 5.99 (d, J = 1.5 Hz, 1H), 5.41 (d,
J = 2.4 Hz, 1H), 5.25 (m, 2H), 5.13 (m, 2H), 5.01 (t, J = 9.6 Hz, 1H), 4.54 (m, 1H),
3.92 (m, 1H), 3.58 (m, 1H), 3.48 (m, 2H), 2.17 (s, 3H), 2.11 (s, 3H), 2.07 (s, 3H),
2.05 (s, 3H), 1.99 (s, 3H), 1.71 (s, 3H), 1.22 (m, 12H); 13C NMR (100 MHz, CDCl3) d
173.3, 170.3, 170.0, 169.8, 169.7, 123.9, 97.1, 90.7, 76.7, 70.5, 70.4, 69.1, 69.0,
68.7, 68.6, 68.5, 43.4, 24.7, 22.4, 22.0, 20.8, 20.7, 20.6, 17.5, 17.4; HRMS (MALDI)
m/z calcd for C29H42O17Na [M+Na]+ 685.2310, found 685.2314.
data; some selected data are shown below. 3: ½a D24
ꢂ
+59.6 (c 1.0, CHCl3); 1H NMR
(400 MHz, CDCl3) d 7.83 (m, 8H), 7.32 (m, 12H), 5.93 (t, J = 9.2 Hz, 1H), 5.90 (d,
J = 8.0 Hz, 1H), 5.69 (m, 2H), 5.21 (br s, 1H), 4.48 (dd, J = 2.0, 11.6 Hz, 1H), 4.40
(dd, J = 5.2, 12.4 Hz, 1H), 4.21 (m, 1H), 3.07 (m, 1H), 2.72 (m, 1H), 0.90, 0.87, 0.77,
0.74, 0.68, 0.67, 0.39 (s, each 3H); 13C NMR (100 MHz, CDCl3) d 175.7, 166.0,
165.6, 165.1, 164.7, 142.9, 133.4, 133.3, 133.2, 133.0, 129.9, 129.8, 129.7, 129.6,
128.6, 128.4, 128.3, 122.7, 91.9, 78.8, 72.9, 72.8, 70.4, 69.3, 62.7, 55.1, 47.4, 46.8,