Synthesis of a novel D-glucose-conjugated 15-crown-5 ether with a spiro ketal structure.
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.
Yamanoi
Takashi
T
The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. tyama@noguchi.or.jp
Oda
Yoshiki
Y
Muraishi
Hitomi
H
Matsuda
Sho
S
D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans; D005947:Glucose / Q000737:chemistry*; D005960:Glucosides; D006031:Glycosylation; D013141:Spiro Compounds
D043844:Crown Ethers; D005663:Furans; D005960:Glucosides; D013141:Spiro Compounds; C520774:spiroketal; C027792:vinyl glucopyranoside; C042148:15-crown-5; D005947:Glucose
Org Biomol Chem. 2004 May 7;2(9):1395-403
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