O. Arjona et al. / Tetrahedron Letters 42 (2001) 7041–7043
7043
4. (a) Lundt, I.; Wagner, S. H. J. Chem. Soc., Perkin Trans.
1 2001, 780; (b) Carpintero, M.; Ferna´ndez-Mayoralas,
A.; Jime´nez-Barbero, J. Eur. J. Org. Chem. 2001, 681; (c)
Arjona, O.; Iradier, F.; Medel, R.; Plumet, J. Tetrahedron
Asymmetry 1999, 10, 3431.
5. (a) Acen˜a, J. L.; Arjona, O.; Man˜as, R.; Plumet, J. J.
Org. Chem. 2000, 65, 2580; (b) Acen˜a, J. L.; Arjona, O.;
Plumet, J. J. Org. Chem. 1997, 62, 3360; (c) Acen˜a, J. L.;
Arjona, O.; Ferna´ndez de la Pradilla, R.; Plumet, J.;
Viso, A. J. Org. Chem. 1994, 59, 6419; (d) Acen˜a, J. L.;
Arjona, O.; Ferna´ndez de la Pradilla, R.; Plumet, J.;
Viso, A. J. Org. Chem. 1992, 57, 1945.
2.11 (s, 3H, COCH3), 2.41–2.38 (m, 1H, H-5), 3.87 (dd,
1H, J=6.0, 10.8 Hz, CH2O), 3.96 (dd, 1H, J=9.0, 11.4
Hz, CH2O), 5.12 (td, 1H, J=3.0, 10.2 Hz, H-3), 5.28 (t,
1H, J=3.0 Hz, H-1), 5.00 (bs, 1H, H-4). 13C NMR
(CDCl3, 75 MHz): l 20.8, 20.9, 21.3, 26.7, 29.7, 33.6,
63.4, 67.5, 68.4, 68.5, 170.2, 170.2, 170.3, 170.9. IR
(CHCl3): w 2960, 2928, 1736, 1647 cm−1. Anal. calcd for
C15H22O8: C, 54.54; H, 6.67. Found: C, 54.68; H, 6.82.
10. Data for: 1,2,4,6-tetra-O-acetyl-3-deoxy-5a-carba-a-DL
-
1
glucopyranose, 16: H NMR (CDCl3, 300 MHz): l 1.59
(ddd, 1H, J=2.4, 13.2, 15.6 Hz, H-6), 2.01 (s, 3H,
COCH3), 2.06 (s, 3H, COCH3), 2.07 (s, 3H, COCH3),
2.08–1.84 (m, 3H, 2 H-3 and H-5), 2.13 (s, 3H, COCH3),
2.20–2.11 (m, 1H, H-6), 3.97 (dd, 1H, J=3.0, 11.1 Hz,
CH2O), 4.13 (dd, 1H, J=4.8, 11.1 Hz, CH2O), 4.79 (td,
1H, J=4.8, 11.1 Hz, H-1), 4.86 (ddd, 1H, J=3.0, 4.5,
12.3 Hz, H-2), 5.35 (bs, H-1). 13C NMR (CDCl3, 75
MHz): l 20.8, 21.0, 21.1, 29.2, 29.7, 30.9, 35.3, 63.5, 67.6,
69.3, 170.0, 170.1, 170.9. IR (CHCl3): w 2926, 2854, 1740
cm−1. Anal. calcd for C15H22O8: C, 54.54; H, 6.67.
Found: C, 54.67; H, 6.80.
6. (a) Nicotra, F. In Carbohydrate Chemistry; Boons, J.,
Ed.; Blackie, 1998; (b) Collins, P.; Ferrier, R.
Monosacharides; Wiley, 1995.
7. Acen˜a, J. L.; Arjona, O.; Ferna´ndez de la Pradilla, R.;
Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906.
8. Data for: 1,3,4,6-tetra-O-acetyl-2-deoxy-5a-carba-a-DL
-
allopyranose, 8: 1H NMR (CDCl3, 300 MHz): l 1.70
(ddd, 1H, J=3.4, 11.2, 14.6 Hz, H-6), 1.85 (dt, 1H,
J=3.4, 15.6 Hz, H-2), 2.04–2.00 (m, 1H, H-6), 2.04 (s,
3H, COCH3), 2.07 (s, 6H, 2COCH3), 2.08 (s, 3H,
COCH3), 2.27 (dd, 1H, J=2.4, 15.6 Hz, H-2), 2.63–2.54
(m, 1H, H-5), 4.01 (dd, 1H, J=3.4, 11.2 Hz, CH2O), 4.20
(dd, 1H, J=4.9, 11.2 Hz, CH2O), 4.90 (dd, 1H, J=2.9,
10.3 Hz, H-4), 5.05 (t, 1H, J=3.4 Hz, H-1), 5.30 (d, 1H,
J=3.4 Hz, H-3). 13C NMR (CDCl3, 75 MHz): l 20.8,
21.1, 21.3, 29.7, 31.5, 31.7, 63.7, 67.1, 68.0, 70.7, 170.2,
170.9. IR (CHCl3): w 2962, 2928, 1736, 1711 cm−1. Anal.
calcd for C15H22O8: C, 54.54; H, 6.67. Found: C, 54.70;
H, 6.80.
Data for: 1,2,4,6-tetra-O-acetyl-3-deoxy-5a-carba-b-DL
-
1
mannopyranose, 17: H NMR (CDCl3, 300 MHz): l 1.66
(ddd, 1H, J=2.7, 10.8, 13.7 Hz, H-6), 2.03 (s, 3H,
COCH3), 2.06 (s, 3H, COCH3), 2.08 (s, 3H, COCH3),
2.11–1.77 (m, 3H, 2H-3 and H-5), 2.14 (s, 3H, COCH3),
2.27 (dt, 1H, J=4.5, 13.9 Hz, H-6), 4.09 (m, 2H, CH2O),
4.93 (ddd, 1H, J=2.5, 4.5, 11.1 Hz, H-1), 5.02–4.97 (m,
1H, H-4), 5.37 (bs, 1H, H-4). 13C NMR (CDCl3, 75
MHz): l 21.2, 21.4, 21.5, 27.8, 30.1, 33.6, 39.7, 64.8, 68.7,
68.9, 70.7, 170.5, 170.7, 171.3. IR (CHCl3): w 2930, 2854,
1739 cm−1. Anal. calcd for C15H22O8: C, 54.54; H, 6.67.
Found: C, 54.42; H, 6.79.
9. Data for: 1,3,4,6-tetra-O-acetyl-2-deoxy-5a-carba-a-DL
-
galactopyranose, 10: 1H NMR (CDCl3, 300 MHz): l
1.63–1.58 (m, 1H, H-6), 1.73 (dt, 1H, J=2.9, 14.2 Hz,
H-6), 1.95 (dd, 2H, J=2.9, 9.3 Hz, 2H-2), 2.00 (s, 3H,
COCH3), 2.05 (s, 3H, COCH3), 2.08 (s, 3H, COCH3),
11. Ogawa, S.; Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.;
Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. 1 1985,
903.