Towards the preparation of 2"-deoxy-2"-fluoro-adenophostin A. Study of the glycosylation reaction

被引：17

作者：

Benito, David ^{[1
]}

Matheu, M. Isabel ^{[1
]}

Morere, Alain ^{[2
,3
]}

Diaz, Yolanda ^{[1
]}

Castillon, Sergio ^{[1
]}

机构：

[1] Univ Rovira & Virgili, Fac Quim, Dept Quim Analit & Quim Organ, Tarragona 43007, Spain

[2] Univ Montpellier 1, Ecole Natl Super Chim Montpellier, CNRS, IBMM,UMR 5247, F-34296 Montpellier 05, France

[3] Univ Montpellier 2, Ecole Natl Super Chim Montpellier, CNRS, IBMM,UMR 5247, F-34296 Montpellier 05, France

来源：

TETRAHEDRON | 2008年 / 64卷 / 48期

关键词：

D O I：

10.1016/j.tet.2008.09.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2 ''-deoxy-2 ''-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2 ''-deoxy-2 ''-fluoroglycoside with excellent alpha-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10906 / 10911

页数：6

共 72 条

[1] The reaction of pyranoside 2-uloses with DAST revised.: Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols [J].

Aghmiz, ML ;

Díaz, Y ;

Jana, GH ;

Matheu, MI ;

Echarri, R ;

Castillón, S ;

Jimeno, ML .

TETRAHEDRON, 2001, 57 (31) :6733-6743

[2] RADICAL CYCLIZATION ROUTES TO BRIDGED PYRANOSIDES AS PRECURSORS OF DENSELY FUNCTIONALIZED CYCLOALKANES [J].

ALONSO, RA ;

VITE, GD ;

MCDEVITT, RE ;

FRASERREID, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :573-584

[3] An improved synthesis of 4-O-benzoyl-2,2-difluorooleandrose from L-rhamnose.: Factors determining the synthesis of 2,2-difluorocarbohydrates from 2-uloses [J].

Barrena, MI ;

Matheu, MI ;

Castillón, S .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2184-2188

[4] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[5] Design, synthesis and biological evaluation of hetaryl-nucleoside derivatives as inhibitors of chitin synthase [J].

Behr, JB ;

Gourlain, T ;

Helimi, A ;

Guillerm, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) :1713-1716

[6] Sc(OTf)3 as efficient catalyst for aryl C-glycoside synthesis [J].

Ben, A ;

Yamauchi, T ;

Matsumoto, T ;

Suzuki, K .

SYNLETT, 2004, (02) :225-230

[7]

BONJOUKLIAN R, 1990, Patent No. [376518, 0376518]

[8] A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor [J].

Burkart, MD ;

Zhang, ZY ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11743-11746

[9] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].

DAVID, S ;

HANESSIAN, S .

TETRAHEDRON, 1985, 41 (04) :643-663

[10] Synthesis of deoxyfluoro sugars from carbohydrate precursors [J].

Dax, K ;

Albert, M ;

Ortner, J ;

Paul, BJ .

CARBOHYDRATE RESEARCH, 2000, 327 (1-2) :47-86

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