Preparation of methyl 2,3-di-Ο-mesyl-4,6-thioanhydro-α-D-galactopyranoside and methyl 2-Ε-mesyl-4,6-thioanhydro-α-D-gulopyranoside

Carbohydrate Research

Volumn 325, Issue 4, 2000, Pages 237-244

  Adiwidjaja, Gunadi ^a   Brunck, Jörg Stephan ^a   Polchow, Kerstin ^a   Voss, Jürgen ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

2 Oxa 7 thiabicyclo 4.2.0 octanes; 1C4 D gulopyranose derivative; Mitsunobu reaction; Thiosugars; X ray diffraction analysis

Indexed keywords

ACETIC ACID DERIVATIVE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; GALACTOSE; METHYL 2 O MESYL 4,6 THIOANHYDROGULOPYRANOSIDE; METHYL 2,3 DI O MESYL 4,6 THIOANHYDROGALACTOPYRANOSIDE; METHYL 2,3-DI-O-MESYL-4,6-THIOANHYDROGALACTOPYRANOSIDE; METHYL 2-O-MESYL-4,6-THIOANHYDROGULOPYRANOSIDE; METHYL THIOACETATE; METHYLGLUCOSIDE; OCTANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE; X RAY DIFFRACTION;

ACETATES; BICYCLO COMPOUNDS, HETEROCYCLIC; GALACTOSE; MAGNETIC RESONANCE SPECTROSCOPY; METHYLGLUCOSIDES; MODELS, MOLECULAR; OCTANES; TEMPERATURE; X-RAY DIFFRACTION;

EID: 0034607518     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(00)00009-4     Document Type: Article

References (31)

1. J. Wirsching. J. Voss, Eur. J. Org. Chem., (1999) 691-699.
2. (a) J. Voss, O. Schulze, F. Olbrich, G. Adiwidjaja, Phosphorus, Sulfur, Silicon, 120 (1997) 389-390.
3. (b) O. Schulze, J. Voss, Phosphorus, Sulfur, Silicon, 153-154 (1999) 429-430.
4. (a) O. Mitsunobu, Synthesis, (1981) 1-28.
5. (b) R.P. Volante, Tetrahedron Lett., 22 (1981) 3119-3122.
6. (b) D.L. Hughes, Org. React. (NY), 42 (1992) 335-656.
7. (c) S.H. Kawai, J. Chin, G. Just, Carbohydr. Res., 211 (1991) 245-260.
8. (d) I. Dancy, L. Laupichler, P. Rollin, J. Thiem, Justus Liebigs Ann. Chem., (1993) 343-350.
9. (e) J. Brånalt, I. Kvarnström, B. Classon, B. Samuelsson, J. Org. Chem., 61 (1996) 3604-3610.
10. (f) J. Moravcová, P. Rollin, C. Lorin, V. Gardon, J. Capková, J. Mazáĉ, J. Carbohydr. Chem., 16 (1997) 113-127.
11. D. Camp, I.D. Jenkins, Aust. J. Chem., 43 (1990) 161-168.
12. (a) K. Polchow, Diploma Thesis, University of Hamburg, 1997.
13. (b) J.-S. Brunck, Dissertation, University of Hamburg, 1993.
14. O. Schulze, Diploma Thesis, University of Hamburg, 1995.
15. (a) P. Collins, R. Ferrier, Monosaccharides. Their Chemistry and Their Roles in Natural Products, Wiley, Chichester, 1995, p. 194 ff.
16. (b) J. Lehmann, Kohlenhydrate. Chemie und Biologie, Thieme Verlag, Stuttgart, 2. Aufl. 1996, p. 115 f.
17. (c) M. Miljkovic, M. Gligorijevic, D. Glišin, J. Org. Chem., 39 (1974) 3223-3226.
18. (d) A.C. Richardson, Carbohydr. Res., 10 (1969) 395-402 and refs therein.
19. (a) J.K.N. Jones, Can. J. Chem., 34 (1956) 840-842.
20. (b) M.L. Wolfrom, A.B. Diwadkar, J. Gelas, D. Horton, Carbohydr. Res., 35 (1974) 87-96.
21. H.B. Sinclair, Carbohydr. Res., 50 (1976) 247-256.
22. B. Fraser-Reid, B. Boctor, Can. J. Chem., 47 (1969) 393-401.
23. (a) K. Toshima, T. Yoshida, S. Mukaiyama, K. Tatsuta, Carbohydr. Res., 222 (1991) 173-188.
24. (b) K. Toshima, S. Mukaiyama, Y. Nozaki, H. Inokuchi, M. Nakata, K. Tatsuta, J. Am. Chem. Soc., 116 (1994) 9042-9051 and refs. cited therein.
25. I. Izquierdo Cubero, M.T. Plaza Lopez-Espinosa, Carbohydr. Lett., 1 (1995) 191-198.
26. P.W. Austin, J.G. Buchanan, E.M. Oakes, J. Chem. Soc., Chem. Commun., (1965) 374-375.
27. Autorenkollektiv, Organikum, 19th ed., Johann Ambrosius Barth Verlag, Leipzig, 1993, pp. 659-681.
28. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr., 27 (1994) 435.
29. G.M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, Göttingen, Germany, 1997.
30. D. Cremer, J.A. Pople, J. Am. Chem. Soc., 97 (1975) 1354-1358.
31. A.L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1999.