Protection of hydroxy groups with diphenylmethyl and 9-fluorenyl trichloroacetimidates - Effect on anomeric stereocontrol

被引：44
作者：
Ali, IAI
El Ashr, ESH
Schmidt, RR
机构：
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
[2] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 21期
关键词：
carbohydrates; glycosidation; protecting groups; stereoselectivity; trichloroacetimidates;
D O I：
10.1002/ejoc.200300323
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The use of O-diphenylmethyl (DPM) and the O-(9-fluorenyl) (Fl) trichloroacetimidates permitted efficient protection of alcohols. The compatibility of these groups with other chemical manipulations is demonstrated. Glucosylation of typical acceptors with an O-glucopyranosyl trichloroacetimidate as donor having a DPM group at 2-O afforded beta-glucopyranosides, thus demonstrating anchimeric assistance of the DPM group in the anomeric stereocontrol. This effect was also observed in mannopyranoside synthesis. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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收藏
页码：4121 / 4131
页数：11
相关论文
共 48 条
[1]   BENZHYDRYL ESTERS OF AMINO ACIDS IN PEPTIDE SYNTHESIS [J].
ABODERIN, AA ;
DELPIERRE, GR ;
FRUTON, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (23) :5469-+
[2]  
AVERBACK P, 1998, CHEM ABSTR, V130, P38192
[3]  
BOITON R, 1964, J CHEM SOC, P1895
[4]   STERIC EFFECTS ON ACIDITIES OF 9-ALKYLFLUORENES, 9-(ALKYLTHIO)FLUORENES, AND 9-ALKOXYFLUORENES AND ON THE ELECTRON-TRANSFER ABILITIES OF THEIR CONJUGATE BASES [J].
BORDWELL, FG ;
BAUSCH, MJ ;
WILSON, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5465-5470
[5]   THE REACTION OF DIPHENYLCARBENE WITH NITROXIDES [J].
CASAL, HL ;
WERSTIUK, NH ;
SCAIANO, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5214-5217
[6]  
CASTROPALOMIN JC, 1998, THESIS U KONSTANZ
[7]   IMIDOESTER .1. DARSTELLUNG VON TRICHLORACETIMIDSAUREESTERN [J].
CRAMER, F ;
PAWELZIK, K ;
BALDAUF, HJ .
CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (05) :1049-1054
[8]   THE SYNTHESIS OF 7-ALKOXYINDOLES [J].
DOBSON, D ;
TODD, A ;
GILMORE, J .
SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :611-617
[9]   SUBSTITUENT EFFECTS IN FLUORENE COMPOUNDS .3. HYDROLYSIS OF 9-CHLORO-9-PHENYLFLUORENES [J].
EABORN, C ;
GOLESWOR.RC ;
LILLY, MN .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JUL) :3052-&
[10]   SELECTIVE CLEAVAGE OF ANOMERIC ACETYL GROUPS OF ACETYLATED GLYCOSYL RESIDUES BY HYDRAZINE [J].
EXCOFFIER, G ;
GAGNAIRE, D ;
UTILLE, JP .
CARBOHYDRATE RESEARCH, 1975, 39 (02) :368-373
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