Synthesis of C-glucoside endo-glycals from C-glucosyl vinyl sulfones

被引:11
作者
Gueyrard, D [1 ]
Fontaine, P [1 ]
Goekjian, PG [1 ]
机构
[1] Univ Lyon 1, CNRS, UMR 5181, Lab Chim Organ 2, F-69622 Villeurbanne, France
来源
SYNTHESIS-STUTTGART | 2006年 / 09期
关键词
vinyl sulfones; C-glycosides; exo-glycals; ipso substitution;
D O I
10.1055/s-2006-926422
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and the reactivity of C-glucosyl vinyl sultones in two steps from benzylated gluconolactone and benzothiazolylsulfones derivatives is reported.
引用
收藏
页码:1499 / 1503
页数:5
相关论文
共 22 条
[1]   Synthetic approaches to C-glucosinolates [J].
Aucagne, V ;
Gueyrard, D ;
Tatibouët, A ;
Quinsac, A ;
Rollin, P .
TETRAHEDRON, 2000, 56 (17) :2647-2654
[2]   CONVERSION OF 2,6-ANHYDRO-1-DEOXY-D-GALACTO-HEPT-1-ENITOL INTO 1-DEOXY-D-GALACTO-HEPTULOSE BY BETA-D-GALACTOSIDASE [J].
BROCKHAUS, M ;
LEHMANN, J .
CARBOHYDRATE RESEARCH, 1977, 53 (01) :21-31
[3]   Toward partial fucosyl transferase transition state analogues:: methylene sulfono sulfonamide as surrogate of pyrophosphate [J].
Carchon, G ;
Chrétien, F ;
Chapleur, Y .
TETRAHEDRON LETTERS, 2003, 44 (30) :5715-5718
[4]   Studies on the synthesis of C-glycoside sulfones as potential glycosyl transferase inhibitors [J].
Gervay, J ;
Flaherty, TM ;
Holmes, D .
TETRAHEDRON, 1997, 53 (48) :16355-16364
[5]  
GOEKJIAN PG, 2003, CARBOHYDRATE BASED D, P305
[6]   Synthesis of methylene exoglycals using a modified Julia olefination [J].
Gueyrard, D ;
Haddoub, R ;
Salem, A ;
Bacar, NS ;
Goekjian, PG .
SYNLETT, 2005, (03) :520-522
[7]   A new intramolecular migration in thiosugar chemistry:: S→O transfer of a benzothiazol-2-yl group in saccharidic sulfones [J].
Gueyrard, D ;
Lorin, C ;
Moravcova, J ;
Rollin, P .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1999, 18 (03) :317-331
[8]   NITROUS-ACID DEAMINATION OF GLYCOSIDES AND ACETATES OF 2-AMINO-2-DEOXY-D-GLUCOSE [J].
HORTON, D ;
PHILIPS, KD .
CARBOHYDRATE RESEARCH, 1973, 30 (02) :367-374
[9]   FACILE INTRAMOLECULAR ACYLATION REACTIONS OF GAMMA-(ACYLOXY)SULFONES AND DELTA-(ACYLOXY)SULFONES - SYNTHESIS OF SUBSTITUTED CHIRAL DIHYDROFURANS AND DIHYDROPYRANS [J].
JACOBS, HK ;
GOPALAN, AS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) :2014-2019
[10]  
KAYE A, 1988, TETRAHEDRON LETT, V29, P141