Synthesis of α,α-, α,β-, and β,β-(dimaltoside)s of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol: A proposal for an initial adhesion mode

Carbohydrate Research

Volumn 311, Issue 1-2, 1998, Pages 11-24

  Tsuzuki, Mina ^a   Tsuchiya, Tsutomu ^a  

^a Institute of Bio Organic Chemistry   (Japan)

Author keywords

Adhesion; Butane 1,4 diol; Dimaltoside; Ethane 1,2 diol; Maltoside; Propane 1,3 diol

Indexed keywords

1,3 BUTANEDIOL; ALPHA,ALPHA BUTANE 1,4 DIO DIMALTOSIDE; ALPHA,ALPHA ETHANE 1,2 DIOL DIMALTOSIDE; ALPHA,ALPHA PROPANE 1,3 DIOL DIMALTOSIDE; ALPHA,BETA BUTANE 1,4 DIOL DIMALTOSIDE; ALPHA,BETA ETHANE 1,2 DIOL DIMALTOSIDE; ALPHA,BETA PROPANE 1,2 DIOL DIMALTOSIDE; BETA,BETA BUTANE 1,2 DIOL DIMALTOSIDE; BETA,BETA ETHANE 1,2 DIOL DIMALTOSIDE; BETA,BETA PROPANE 1,3 DIOL DIMALTOSIDE; ETHYLENE GLYCOL; PROPYLENE GLYCOL; UNCLASSIFIED DRUG;

ADHESION; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; TECHNIQUE;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROPANOLS; SUGAR ALCOHOLS;

EID: 0031656558     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00191-8     Document Type: Article

References (29)

1. (a) A. Varki, Proc. Natl. Acad. Sci. USA, 91 (1994) 7390-7397;
2. (b) A. Noy, C.D. Frisbie, L.F. Rozsnyai, M.S. Wrighton, and C.M. Lieber, J. Am. Chem. Soc., 117 (1995) 7943-7951;
3. (c) S.A. DeFrees, L. Phillips, L. Guo, and S. Zalipsky, J. Am. Chem. Soc., 118 (1996) 6101-6104.
4. M.L. Smythe and M. von Itzstein, J. Am. Chem. Soc., 116 (1994) 2725-2733.
5. W. Verboom, D.M. Rudkevich, and D.N. Reinhoudt, Pure & Appl. Chem., 66 (1994) 679-686.
6. C.-Y. Huang, L.A. Cabell, and E.V. Anslyn, J. Am. Chem. Soc., 116 (1994) 2778-2792.
7. M. Nishio and M. Hirota, Tetrahedron, 45 (1989) 7201-7245.
8. P.A. Finan and C.D. Warren, J. Chem. Soc., (1962) 2823-2824; A.J. Freestone, L. Hough, and A.C. Richardson, Carbohydr. Res., 28 (1973) 378-386.
9. P.A. Finan and C.D. Warren, J. Chem. Soc., (1962) 2823-2824; A.J. Freestone, L. Hough, and A.C. Richardson, Carbohydr. Res., 28 (1973) 378-386.
10. B. Classon, P.J. Garegg, and B. Samuelsson, Acta Chem. Scand. B, 38 (1984) 419-422.
11. K. Igarashi, Adv. Carbohydr. Chem. Biochem., 34 (1977) 243-283.
12. Y. Oikawa, T. Yoshioka, and O. Yonemitsu, Tetrahedron Lett., 23 (1982) 885-888.
13. R. Johansson and B. Samuelsson, J. Chem. Soc. Perkin Trans. I, (1984) 2371-2374.
14. (a) H.H. Bosshard, R. Mory, M. Schmid, and H. Zollinger, Helv. Chem. Acta, 42 (1959) 1653-1658;
15. (b) T. Iversen and D.R. Bundle, Carbohydr. Res., 103 (1982) 29-40.
16. K. Takeo and T. Imai, Carbohydr. Res., 165 (1987) 123-128.
17. (a) P.J. Garegg, H. Hultberg, and C. Lindberg, Carbohydr. Res., 83 (1980) 157-162;
18. (b) T. Ogawa, S. Nakabayashi, and T. Kitajima, Carbohydr. Res., 114 (1983) 225-236.
19. (a) P. Konradsson, U.E. Udodong, and B. Fraser-Reid, Tetrahedron Lett., 31 (1990) 4313-4316;
20. (b) M. Sasaki, K. Tachibana and H. Nakanishi, Tetrahedron Lett., 32 (1991) 6873-6876;
21. (c) K. Toshima and K. Tatsuta, Chem. Res. 93 (1993) 1503-1531.
22. R.R. Schmidt and W. Kinzy, Adv. Carbohydr. Chem. Biochem., 50 (1994) 21-123.
23. Y. Takahashi, T. Tsuchiya, S. Umezawa, and H. Umezawa, Carbohydr Res., 210 (1991) 221-232.
24. C.M. McCloskey, Adv. Carbohydr. Chem., 12 (1957) 137-156.
25. (a) P.V. Demarco and A.L. Thakkar, J. Chem. Soc. Chem. Commun., (1970) 2-4;
26. (b) D.J. Wood, F.E. Hruska, and W. Saenger, J. Am. Chem. Soc., 99 (1977) 1735-1740;
27. (c) Y. Inoue, T. Okada, Y. Miyata, and R. Chûjô, Carbohydr. Res., 125 (1984) 65-76;
28. (d) Y. Kanda, Y. Yamamoto, Y. Inoue, R. Chûjô, and S. Kobayashi, Bull. Chem. Soc. Jpn., 62 (1989) 2002-2008.
29. H. Günther, NMR Spectroscopy, Basic Principles, Concepts, and Applications in Chemistry, 2nd ed., John Wiley & Sons, Chichester, UK, 1996, pp 78-93.