9076
J. Frigell, I. Cumpstey / Tetrahedron Letters 48 (2007) 9073–9076
DC, 2005; pp 275–285; (b) Crick, D. C.; Mahapatra, S.;
Brennan, P. J. Glycobiology 2001, 11, 107R–118R.
Ko¨ll, P.; John, H.-G.; Schulz, J. Liebigs Ann. Chem. 1982,
613–625.
2. (a) Lee, R. E.; Smith, M. D.; Pickering, L.; Fleet, G. W. J.
Tetrahedron Lett. 1999, 40, 8689–8692; (b) Lee, R. E.;
Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.;
Grewal, R. K.; Yah, W.; Besra, G. S.; Brennan, P. J.;
Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733; (c)
Liautard, V.; Christina, A. E.; Desvergnes, V.; Martin, O.
R. J. Org. Chem. 2006, 71, 7337–7345; (d) Liautard, V.;
Desvergnes, V.; Martin, O. R. Org. Lett. 2006, 8, 1299–
1302.
14. The acetonide ring sizes were assigned based on the
chemical shifts for the acetonide carbons, as described in
Ref. 12. Relevant data for 7 (5-membered ring): 27.1, 27.1
(2 · q, C(CH3)2), 109.3 (s, C(CH3)2); 8 (7-membered ring):
24.4, 25.2 (2 · q, C(CH3)2), 101.5 (s, C(CH3)2);
9
(6-membered ring): 19.4, 29.7 (2 · q, C(CH3)2), 99.7 (s,
C(CH3)2)
3. (a) Ghavami, A.; Chen, J. J.-W.; Pinto, B. M. Carbohydr.
Res. 2004, 339, 401–407; (b) Randell, K. D.; Johnston, B.
D.; Pinto, B. M. Carbohydr. Res. 2000, 326, 145–150; (c)
Randell, K. D.; Johnston, B. D.; Lee, E. E.; Pinto, B. M.
Tetrahedron: Asymmetry 2000, 11, 207–222.
O
O
O
O
BnO
BnO
BnO
OBn OBn OH
BnO
OH
4. (a) Owen, D. J.; Thomson, R. J.; von Itzstein, M.
Carbohydr. Res. 2002, 337, 2017–2022; (b) Kovensky, J.;
Cirelli, A. F.; Sinay, P. Carbohydr. Lett. 1999, 3, 271–276;
(c) Kovensky, J.; McNeil, M.; Sinay, P. J. Org. Chem.
1999, 64, 6202–6205; (d) Caravano, A.; Mengin-Lecreulx,
D.; Brondello, J.-M.; Vincent, S. P.; Sinay, P. Chem. Eur.
J. 2003, 9, 5888–5898.
5. Rose, N. L.; Completo, G. C.; Lin, S.-J.; McNeil, M.;
Palcic, M. M.; Lowary, T. L. J. Am. Chem. Soc. 2006, 128,
6721–6729.
6. McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org.
Chem. 1966, 31, 1516–1521.
7. (a) Horneman, A. M.; Lundt, I. J. Org. Chem. 1998, 63,
1919–1928; (b) Horneman, A. M.; Lundt, I. Synthesis
1999, 317–325.
8. (a) Callam, C. S.; Lowary, T. L. J. Org. Chem. 2001, 66,
8961–8972; (b) Callam, C. S.; Lowary, T. L. Org. Lett.
2000, 2, 167–169.
9. Seepersaud, M.; Al-Abed, Y. Tetrahedron Lett. 2000, 41,
7801–7803.
10. Cumpstey, I. Tetrahedron Lett. 2005, 46, 6257–6259.
11. Numbering of carbohydrates 2, 3, 5 and 6 and carbasugars
1, 13 and 15–21 is according to the carbohydrate conven-
tion. Polyhydroxylated open chain derivatives 4, 7–12 and
14 are, for simplicity, numbered using the same numbering
scheme as shown in Scheme 2.
8
9
15. Sajiki, H.; Hirota, K. Tetrahedron 1998, 54, 13981–13996.
16. Characterisation data for 4a-carba-b-D-galactofuranose 1:
25
½aꢁD ꢀ15.6 (c, 1.0 in CH3OH); dH (400 MHz, CD3OD)
1.67 (1H, m, H-4a), 1.96–2.05 (2H, m, H-4, H-4a0), 3.51
0
0
(1H, dd, J5,6 7.8 Hz, J6,6 11.7 Hz, H-6), 3.62 (1H, dd, J5,6
4.2 Hz, J6,6 11.7 Hz, H-60), 3.71–3.79 (3H, m, H-2, H-3,
H-5), 3.90 (1H, m, H-1); dC (100.6 MHz, CD3OD) 30.5 (t,
C-4a), 45.1 (d, C-4), 66.4 (t, C-6), 73.5, 78.4, 85.5 (3 · d,
C-2, C-3, C-5), 75.5 (d, C-1); HRMS calcd for C7H14O5Na
(MNa+) 201.0733. Found 201.0728.
0
17. Characterisation data for 1,2,3,5,6-penta-O-acetyl-4a-car-
ba-b-D-galactofuranose 18: dH (400 MHz, CDCl3) 1.90
0
(1H, ddd, J1,4a 2.4 Hz, J4,4a 8.6 Hz, J4a,4a 14.5 Hz, H-4a),
2.05, 2.06, 2.06, 2.07, 2.10 (15H, 5 · s, 5 · CH3), 2.17 (1H,
m, H-4a0), 2.54 (1H, ddat, J 4.6 Hz, J 8.6 Hz, J 11.2 Hz,
0
H-4), 4.01 (1H, dd, J5,6 6.5 Hz, J6,6 11.9 Hz, H-6), 4.21
(1H, dd, J5,6 4.2 Hz, J6,6 11.9 Hz, H-60), 5.02 (1H, m,
H-3), 5.04 (1H, m, H-1), 5.17 (1H, m, H-5), 5.20 (1H, m,
H-2); dC (100.6 MHz, CDCl3) 20.9, 21.0, 21.0, 21.0, 21.2
(5 · q, 5 · CH3), 29.5 (t, C-4a), 41.8 (d, C-4), 64.0 (t, C-6),
69.4 (d, C-5), 75.3 (d, C-1), 76.6 (d, C-3), 81.1 (d, C-2),
170.3, 170.5, 170.7 (3 · s, 5 · C@O); IR (film) 1743 (s,
OC@O) cmꢀ1; HRMS calcd for C17H24O10Na (MNa+)
411.1262. Found 411.1251 (‘at’ refers to apparent triplet).
18. (a) Marschner, C.; Baumgartner, J.; Griengel, H. J. Org.
Chem. 1995, 60, 5224–5235; (b) Tadano, K.-I.; Hakuba,
K.; Kimura, H.; Ogawa, S. J. Org. Chem. 1989, 54, 276–
279.
0
0
12. Grindley, T. B.; Cote, C. J. P.; Wickramage, C. Carbo-
hydr. Res. 1985, 140, 215–238.
13. (a) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R.
Tetrahedron 1989, 45, 327–336; (b) Zhang, Y.-M.; Mallet,
J.-M.; Sinay, P. Carbohydr. Res. 1992, 236, 73–88; (c)