Journal of the Korean Wood Science and Technology

The Korean Society of Wood Science & Technology (한국목재공학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Octopus Type Trimethylene Glycol β-D-glucopyranosides

  • Kim, Yong Sik (Div. of Wood Chemistry & Microbiology, Dept. of Forest Products, Korea Forest Research Institute) ;
  • Kadla, John F. (Biomaterials Chemistry, Faculty of Forestry, University of British Columbia)
  • Received : 2013.02.20
  • Accepted : 2013.03.24
  • Published : 2013.03.25
Download PDF
⟨ Previous Next ⟩

Abstract

The octopus type oligo-hydroxypropylene glycol ${\beta}$-D-glucopyranosides were successfully synthesized in this studies: the sterospecific compound of allyl 2, 3, 4, 6-tetra-O-acetyl-${\beta}$-D-glucopyranosides (1) was deacetylated with NaOMe in MeOH lead to allyl-${\beta}$-D-glucopyranoside (2) which was perallylated and followed by hydroboration and subsequent oxidation afforded (3-hydroxy-propyl) 2, 3, 4, 6-tetraO(3-hydroxy-propyl)-${\beta}$-D-glucopyranoside (4). As a result, not only allylpropylene glycol ${\beta}$-D-glucopyranosides (5, 7, and 9) but also hydroxypropylene glycol ${\beta}$-D-glucopyranosides (6, 8, and 10) were synthesized by repeated sequential perallylation followed by hydroboration/oxidation.

Keywords

References

  1. Hanessian. S. 1983. Total Synthesis of Natural Products: The Chiron Approach. Pergamon Press, New York.
  2. Scott. A. I. 1994. Genetically engineered synthesis of natural products. J. Nat. Prod. 57: 557-573. https://doi.org/10.1021/np50107a001
  3. Ferrier R. J. and S. Middleton. 1993. The Conversion of Carbohydrate Derivatives into Functionalized Cyclohexanes and Cyclopentanes. Chem. Rev. 93: 2779-2831. https://doi.org/10.1021/cr00024a008
  4. Dubber M. and T. K. Lindhorst. 1998. Synthesis of octopus glycosides: core molecules for the construction of glycoclusters and carbohydrate-centered dendrimers. Carbohydr. Res. 310: 35-41. https://doi.org/10.1016/S0008-6215(98)00155-4
  5. Dubber M. and T. K. Lindhorst. 2001. Synthesis of a carbohydrate-centered C-glycoside cluster[1]. J. Carbohydr. Chem. 20: 755-760. https://doi.org/10.1081/CAR-100108288
  6. Dubber, M., O. Sperling and T.K. Lindhorst. 2006. Oligomannoside mimetics by glycosylation of octopus glycosides and their investigation as inhibitors of type 1 fimbriaemediated adhesion of Escherichia coli. Org. Biomol. Chem. 4: 3901-3912. https://doi.org/10.1039/b610741a
  7. Kishida, M. and H. Akita. 2005. Simple preparation of phenylpropenoid $\beta$-D-glucopyranoside congeners by Mizoroki-Heck type reaction using organoboron reagents. Tetrahedron 61: 10559-10568. https://doi.org/10.1016/j.tet.2005.08.043
  8. Lu, W.-Y. G.-Q. Lin, H.-L. Yu, A.-M. Tong and J.-H. Xu. 2007. Facile synthesis of alkyl $\beta$-D-glucopyranosides from D-glucose and the corresponding alcohols using fruit seed meals. J. Mol. Catal. B: Enzym. 44: 72-77. https://doi.org/10.1016/j.molcatb.2006.07.007
  9. Koto, S. N. Morishima, K. Takenaka, K. Kanemitsy, N. Shimoura, M. Kase, S. Kojiro, T. Nakamura, T. Kawase and S. Zen. 1989. 2-Methoxyethyl group for protection of reducing hydroxyl group of aldose. Bull. Chem. Soc. Japan 62: 3549-3566. https://doi.org/10.1246/bcsj.62.3549
  10. Z. Szurmai, L. Szabo and A. Liptak. 1989. Diethylene and triethylene glycol spacers for the preparation of neoglycoproteins. Acta Chim. Hung. 126: 259-269.