Dye-sensitized photooxygenation of 2,5-Bis(glycosyl)furans

Letters in Organic Chemistry

Volumn 8, Issue 5, 2011, Pages 309-314

  Cermola, Flavio ^a   Iesce, Maria R ^a   Astarita, Anna ^a   Passananti, Monica ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Endoperoxides; Glycosides; Glycosyl furans; Photooxygenation; Singlet oxygen; Thermal rearrangement

Indexed keywords

EID: 79957981399     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811795685027     Document Type: Article

References (16)

1. Postema, H. D. M. C-Glycoside Synthesis; CRC Press: London, England, 1995.
2. Cermola, F.; Iesce, M. R.; Montella, S. The first dye-sensitized photooxygenation of 2-(C-glycosyl)furans. One-pot stereoselective approach to new carbohydrate derivatives, Lett. Org. Chem. 2004, 1, 271-275.
3. Astarita, A.; Cermola, F.; Iesce, M. R.; Previtera, L. Dye-sensitized photooxygenation of sugar furans: novel bis-epoxide and spirocyclic C-nucleosides, Tetrahedron 2008, 64, 6744-6748.
4. Cermola, F.; Iesce, M. R.; Buonerba, G. Dye-sensitized photooxygenation of furanosyl furans: synthesis of a new pyridazine C-nucleoside, J. Org. Chem. 2005, 70, 6503-6505. (Pubitemid 41076538)
5. Cermola, F.; Iesce, M. R. Dye-sensitized photooxygenation of sugar-furans as synthetic strategy for novel C-nucleosides and functionalized exo-glycals, Tetrahedron, 2006, 62, 10694-10699. (Pubitemid 44488704)
6. Iesce, M. R.; Cermola, F.; Temussi, F. Photooxygenation of heterocycles, Curr. Org. Chem., 2005, 9, 109-139 and references therein. (Pubitemid 40089532)
7. x mimics as E- and P-selectin inhibitors, Med. Res. Rev. 2002, 22, 566-601 and references therein. (Pubitemid 35299534)
8. a) Hiruma, K.; Kajimoto, T.; Weitz-Schmidt, G.; Ollmann, I.; Wong, C.-H. Rational design and synthesis of a 1,1-linked disaccharide that is 5 times as active as Sialyl Lewis X in binding to E-selectin, J. Am. Chem. Soc., 1996, 118, 9265-9270 (Pubitemid 26355120)
9. (b) Cheng, X.; Khan, N.; Mootoo, D. R. Synthesis of the C-glycoside analogue of a novel Sialyl Lewis X mimetic, J. Org. Chem., 2000, 65, 2544-2547.
10. The α-glucosyl furan 1a used as the acceptor has been synthesized by a reported procedure: Schmidt, R. R.; Effenberger, G. OGlycosyl imidates. 29. Reaction of O-(glucopyranosyl) imidates with electron-rich heterocycles. Synthesis of C-glucosides, Liebigs Ann. Chem. 1987, 10, 825-831.
11. H1,H2 = 6.4 Hz.
12. It is used a, b, c, for benzylated glucose, mannose and galactose sugars, respectively, and a', b', c' for the corresponding acetylated ones. The acceptors 1b', 1c' and 1b were prepared by coupling between furan and the imidates 4b', 4c' and 4b, respectively. While 1c' was obtainded only as α-anomer, 1b' was formed as a β.mixture in ca. 1 : 2 molar ratio, probably due to the neighboring-group participation of the acetyl at the C2 after the removal of the leaving group.
13. Theoretical calculations were performed by SPARTAN '08 Quantum Mechanics Program.
14. 3.
15. Wu, H.-J. and Lin, C.-C. First Exclusive Regioselective Fragmentation of Primary Ozonides Controlled by Remote Carbonyl Groups and a New Method for Determining the Regiochemistry of Carbonyl Oxide Formation, J. Org. Chem., 1996, 61, 3820-3828. (Pubitemid 126532671)
16. 2-Tritylfuran has been prepared following the same procedure [14] used for 2-benzylfuran.