Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH

被引:52
作者
Adinolfi, M [1 ]
Iadonisi, A [1 ]
Ravidà, A [1 ]
Schiattarella, M [1 ]
机构
[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy
关键词
glycosyl iodides; orthoesters; glycals; ethylidenes;
D O I
10.1016/j.tetlet.2003.09.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Peracetylated sugars can be efficiently converted into the corresponding 1,2-ethylidenes, -orthoesters, and -glycals via the in situ generation of glycosyl iodides promoted by I-2/Et3SiH. The approach is straightforward and avoids isolation of the sensitive iodinated intermediates. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7863 / 7866
页数:4
相关论文
共 17 条
[1]  
Adinolfi M, 2002, SYNLETT, P269
[2]  
BETANELI VI, 1982, CARBOHYD RES, V107, P285
[3]   Efficient syntheses of β-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides [J].
Bhat, AS ;
Gervay-Hague, J .
ORGANIC LETTERS, 2001, 3 (13) :2081-2084
[4]  
Caputo R, 1999, EUR J ORG CHEM, V1999, P3147
[5]   Convenient, in situ generation of anhydrous hydrogen iodide for the preparation of α-glycosyl iodides and vicinal iodohydrins and for the catalysis of Ferrier glycosylation [J].
Chervin, SM ;
Abada, P ;
Koreeda, M .
ORGANIC LETTERS, 2000, 2 (03) :369-372
[6]   PREPARATION OF GLYCOSYL HALIDES UNDER NEUTRAL CONDITIONS [J].
ERNST, B ;
WINKLER, T .
TETRAHEDRON LETTERS, 1989, 30 (23) :3081-3084
[7]   Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN [J].
Franz, AH ;
Wei, YQ ;
Samoshin, VV ;
Gross, PH .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7662-7669
[8]   Anionic additions to glycosyl iodides: Highly stereoselective syntheses of beta-, C-, N-, and O-glycosides [J].
Gervay, J ;
Hadd, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6961-6967
[9]   Mechanistic studies on the stereoselective formation of glycosyl iodides: First characterization of beta-D-glycosyl iodides [J].
Gervay, J ;
Nguyen, TN ;
Hadd, MJ .
CARBOHYDRATE RESEARCH, 1997, 300 (02) :119-125
[10]   Glycosyl iodides are highly efficient donors under neutral conditions [J].
Hadd, MJ ;
Gervay, J .
CARBOHYDRATE RESEARCH, 1999, 320 (1-2) :61-69