Preparation and structural determination of methyl 3-C-p-tolylsulfonyl-2-C-p-tolylthio-β-D-glucopyanoside derivatives and their 5a-carba-DL-analogs having non-chair conformation in solutions

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5711-5714

  Sakakibara, Tohru ^a   Suzuki, Kiyotaka ^a   Sakai, Akiko ^a   Shindo, Miwa ^a   Nagano, Chihiro ^a   Narumi, Shinya ^a   Kajihara, Yasuhiro ^a   Mochizuki, Katsura ^a  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

Author keywords

Boat form; Sulfonyl sugars; X ray analysis; D glucopyranoside

Indexed keywords

GLUCOPYRANOSIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; EPIMERIZATION; NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0038505235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01302-9     Document Type: Article

References (15)

1. For example, see: Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990; Part A, Chapter 3.
2. 3 conformation is assigned for a α-D-glucopyranosyl-1-pyridinium salt. See: Hosie, L.; Marshall, P. J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1984, 1121-1131. However, we could not find a paper (except Ref. 6) describing that a non-chair conformer is stable in the case of β-D-glucopyranoside.
3. 3 conformation is assigned for a α-D-glucopyranosyl-1-pyridinium salt. See: Hosie, L.; Marshall, P. J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1984, 1121-1131. However, we could not find a paper (except Ref. 6) describing that a non-chair conformer is stable in the case of β-D-glucopyranoside.
4. 3 conformation is assigned for a α-D-glucopyranosyl-1-pyridinium salt. See: Hosie, L.; Marshall, P. J.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1984, 1121-1131. However, we could not find a paper (except Ref. 6) describing that a non-chair conformer is stable in the case of β-D-glucopyranoside.
5. Sakakibara, T.; Sakai, A., unpublished data.
6. Sakakibara, T.; Suzuki, K. Part of this work was reported in a preliminary form in the 20th International Carbohydrate Symposium, Hamburg, 2000, Abstracts p. 254.
7. 3,4 9.9 Hz.
8. Suresh C.G., Ravindran B., Rao K.N., Pathak T. Acta Crystallogr. C56:2000;1030-1032.
9. Ravindran B., Deshpande S.G., Pathak T. Tetrahedron. 57:2001;1093-1098.
10. Hosoya T., Ohashi Y., Matsumoto T., Suzuki K. Tetrahedron Lett. 37:1996;663-666.
11. Yamada H., Nakatani M., Ikeda T., Marumoto Y. Tetrahedron Lett. 40:1999;5573-5576.
12. The values are determined by conformational preference of the substituent in monosubstituted cylohexanes at 25°C.
13. Eliel E.L., Wilen S.H., Mander L.N. Stereochemistry of Organic Compounds. 1994;696 John Wiley & Sons, New York.
14. 4,5 9.6 Hz.
15. Gaussian 98, Revision A.9, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.