Glycosylations of Tertiary Alcohols: Synthesis of Fully Protected Disaccharides with Sterically Demanding Groups Attached to the Sugar Core

Abstract

Modified gluco- and galactopyranosides with sterically demanding groups in the 4-position were synthesized. Glycosylation studies of these tertiary alcohols with glycosyl trichloroacet­imidates and glycosyl phosphates were performed. Despite steric hindrance the modified disaccharide moieties could be assembled in moderate yields.

Key words

carbohydrates - glycosylation - steric hindrance - glycosides

References

• 1a Varki A. Glycobiology  1993,  3:  97 
• 1b Lis H. Sharon N. Eur. J. Biochem.  1993,  218:  1 
• 1c Dwek RA. Chem. Rev.  1996,  96:  683 
• 1d Lee YC. Lee RT. Acc. Chem. Res.  1995,  28:  322 
• 1e Werz DB. Seeberger PH. Chem. Eur. J.  2005,  11:  3194 
• 1f Seeberger PH. Werz DB. Nature  2007,  446:  1046 
• 2a Choudhury B. Leoff C. Saile E. Wilkins P. Quinn CP. Kannenberg EL. Carlson RW. J. Biol. Chem.  2006,  281:  27932 
• 2b Oberli MA. Bindschädler P. Werz DB. Seeberger PH. Org. Lett.  2008,  10:  905 
• 3a Karlsson KA. Biochem. Soc. Trans.  1999,  27:  471 
• 3b Karlsson KA. Adv. Exp. Med. Biol.  2001,  491:  431 
• 3c Tamborrini M. Werz DB. Frey J. Pluschke G. Seeberger PH. Angew. Chem. Int. Ed.  2006,  45:  6581 ; Angew. Chem. 2006, 118, 6731
• 3d Seeberger PH. Werz DB. Nature Rev. Drug Discovery  2005,  4:  751 
• 4a Herget S. Toukach PV. Ranzinger R. Hull WE. Knirel YA. von der Lieth C.-W. BMC Struct. Biol.  2008,  8:  35 
• 4b Werz DB. Ranzinger R. Herget S. Adibekian A. von der Lieth C.-W. Seeberger PH. ACS Chem. Biol.  2007,  2:  685 
• 5a Thibodeaux CJ. Melançon CE. Liu H.-w. Nature  2007,  446:  1008 
• 5b Chatterjee D. Bozic C. Aspinall GO. Brennan PJ. J. Biol. Chem.  1988,  263:  4092 
• 6 Qian X. Sujino K. Otter A. Palcic MM. Hindsgaul O. J. Am. Chem. Soc.  1999,  121:  12063 
• For 1-adamantanol as acceptor several examples are known:
• 7a Crich D. Sun S. J. Am. Chem. Soc.  1998,  120:  435 
• 7b Crich D. Yao Q. Org. Lett.  2003,  5:  2189 
• 7c Babu RS. O’Doherty GA. J. Am. Chem. Soc.  2003,  125:  12406 
• 7d Okada Y. Mukae T. Okajima K. Taira M. Fujita M. Yamada H. Org. Lett.  2007,  9:  1573 
• 7e Baek JY. Choi TJ. Jeon HB. Kim KS. Angew. Chem. Int. Ed.  2006,  45:  7436 ; Angew. Chem. 2006, 118, 7596
• 8a Ernst C. Piacenza M. Grimme S. Klaffke W. Carbohydr. Res.  2003,  338:  231 
• 8b Shao H. Ekthawatchai S. Wu S.-H. Zou W. Org. Lett.  2004,  6:  3497 
• 8c Elamparuthi E. Linker T. Org. Lett.  2008,  10:  1361 
• 8d Al-Harrasi A. Reissig H.-U. Angew. Chem. Int. Ed.  2005,  44:  6227 ; Angew. Chem. 2005, 117, 6383
• 8e Yin J. Linker T. Chem. Eur. J.  2009,  15:  49 
• 8f Pfrengle F. Lentz D. Reißig H.-U. Angew. Chem. Int. Ed.  2009,  48:  3165 ; Angew. Chem. 2009, 121, 3211
• 9 Kahne D. Walker S. Cheng Y. van Engen D. J. Am. Chem. Soc.  1989,  111:  6881 
• 10 For an overview, see: Lutz J.-F. Angew. Chem. Int. Ed.  2007,  46:  1018 ; Angew. Chem. 2007, 119, 1036
• 11 For an overview, see: Chinchilla R. Najera C. Chem. Rev.  2007,  107:  874 
• 12 Preuss R. Jung K.-H. Schmidt RR. Liebigs Ann. Chem.  1992,  377 
• 13a Zhu X. Schmidt RR. Angew. Chem. Int. Ed.  2009,  48:  1900 ; Angew. Chem. 2009, 121, 1932
• 13b Codée JDC. Seeberger PH. ACS Symp. Ser.  2007,  960:  150 
• 14 Schmidt RR. Kinzy W. Adv. Carbohydr. Chem. Biochem.  1994,  50:  21 
• 15 The compounds 5a and 5b were synthesized before, but analytical data were not given: Jensen HH. Bols M. Org. Lett.  2003,  5:  3419 
• 16 A mixture of compounds 8a and 8b was synthesized before, but analytical data were not given: Daly SM. Armstrong RW. Tetrahedron Lett.  1989,  30:  5713