Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure

Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure

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...

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Main Authors: Sho Matsuda, Hitomi Muraishi, Yoshiki Oda, Takashi Yamanoi
Format: Article
Language:English
Published: MDPI AG 2008-08-01
Series:Molecules
Subjects:
Crown ether
Spiroketal
1-C-Vinylated glucose
Glycosylation
Online Access:http://www.mdpi.com/1420-3049/13/8/1840/
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spelling doaj-3d7d75cf06194a5785be990ab69686eb2020-11-24T23:10:29ZengMDPI AGMolecules1420-30492008-08-011381840184510.3390/molecules13081840Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal StructureSho MatsudaHitomi MuraishiYoshiki OdaTakashi YamanoiAbstract: 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.http://www.mdpi.com/1420-3049/13/8/1840/Crown etherSpiroketal1-C-Vinylated glucoseGlycosylation
collection DOAJ
language English
format Article
sources DOAJ
author Sho Matsuda
Hitomi Muraishi
Yoshiki Oda
Takashi Yamanoi
spellingShingle Sho Matsuda
Hitomi Muraishi
Yoshiki Oda
Takashi Yamanoi
Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
Molecules
Crown ether
Spiroketal
1-C-Vinylated glucose
Glycosylation
author_facet Sho Matsuda
Hitomi Muraishi
Yoshiki Oda
Takashi Yamanoi
author_sort Sho Matsuda
title Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
title_short Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
title_full Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
title_fullStr Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
title_full_unstemmed Synthesis of a Novel D-Glucose-Conjugated 15-Crown-5 Ether with a Spiro Ketal Structure
title_sort synthesis of a novel d-glucose-conjugated 15-crown-5 ether with a spiro ketal structure
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2008-08-01
description 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.
topic Crown ether
Spiroketal
1-C-Vinylated glucose
Glycosylation
url http://www.mdpi.com/1420-3049/13/8/1840/
work_keys_str_mv AT shomatsuda synthesisofanoveldglucoseconjugated15crown5etherwithaspiroketalstructure
AT hitomimuraishi synthesisofanoveldglucoseconjugated15crown5etherwithaspiroketalstructure
AT yoshikioda synthesisofanoveldglucoseconjugated15crown5etherwithaspiroketalstructure
AT takashiyamanoi synthesisofanoveldglucoseconjugated15crown5etherwithaspiroketalstructure
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