1997年
Synthetic studies on selectin ligands/inhibitors: A systematic synthesis of sulfatide and its higher congeners carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute
JOURNAL OF CARBOHYDRATE CHEMISTRY
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- 巻
- 16
- 号
- 6
- 開始ページ
- 831
- 終了ページ
- 858
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1080/07328309708006543
- 出版者・発行元
- MARCEL DEKKER INC
A systematic synthesis of sulfatide (I) and novel sulfatide analogs (II-VI) carrying 2-(tetradecyl)hexadecyl group as a ceramide substitute is described. The 3-O-, 4-O- and 3,4-di-O-levulinoyl derivatives of galactopyranosyl trichloroacetimidates (1, 12, and 13) were coupled with (2S,3R,4E)-3-O-acetyl-2-octadecanamido-4-octadecene-1,3-diol or 2-(tetradecyl)hexadecan-1-ol. The resulting glycolipids (2, 4, 14, and 15) were each transformed, by selective removal of the levulinoyl group(s), and successive sulfation and de-O-acylation, into the 3-sulfates (I, II), 4-sulfate (III), and 3,4-disulfate (IV). The 6-sulfate (V) was prepared from 2-(tetradecyl)hexadecyl beta-D-galactopyranoside (21) via the 6-O-t-butyldimethylsilyl derivative, while the 3'-sulfate of 2-(tetradecyl)hexadecyl beta-D-lactoside (VI) was synthesized from 2-(trimethylsilyl)ethyl 3'-O-benzyl-beta-D-lactoside (26). The structures of the sulfated glycolipids (I-VI) were characterized by ion-spray MS, MS/MS, and H-1 NMR spectrometry.
- リンク情報
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- DOI
- https://doi.org/10.1080/07328309708006543
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:A1997XR83100007&DestApp=WOS_CPL
- URL
- http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=0031504106&origin=inward
- ID情報
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- DOI : 10.1080/07328309708006543
- ISSN : 0732-8303
- Web of Science ID : WOS:A1997XR83100007