synthesis of a novel d-glucose-conjugated 15-crown-5 ether with a spiro ketal structure合成一种新型d-glucose-conjugated 15-crown-5醚与斯皮罗缩酮的结构.pdfVIP

Molecules 2008, 13, 1840-1845 manuscripts; DOI: 10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /molecules Article Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure Takashi Yamanoi *, Yoshiki Oda, Hitomi Muraishi and Sho Matsuda The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan; E-mails: odayoshiki@noguchi.or.jp (Yoshiki Oda), hitommy-heart@bridge.ocn.ne.jp (Hitomi Muraishi), s.matsuda@noguchi.or.jp (Sho Matsuda) * Author to whom correspondence should be addressed. E-mail: tyama@noguchi.or.jp; Fax: (+81) 3 5944 3213. Received: 18 July 2008; in revised form: 12 August 2008 / Accepted: 19 August 2008 / Published: 22 August 2008 Abstract: This paper describes a synthetic approach to a novel D-glucose-conjugated 15- crown-5 ether having a spiroketal structure starting from a 1-C-vinylated glucose derivative. The approach consists of the glycosylation of the vinylated glucose derivative to give an ethyleneoxy spacer derivative using bismuth(III) triflate, the conversion of the 1-C-vinyl group of the glucoside produced into a carboxylic acid group, and the intramolecular condensation between the carboxyl group and the terminal hydroxyl group in the ethyleneoxy spacer. A D-glucose-conjugated 15-crown-5 ether having a unique spiroketal structure was thus successfully synthesized. Keywords: Crown ether; Spiroketal; 1-C-Vinylated glucose; Glycosylation Introduction Crown ether molecules with sacchari