Stereoselective entry to β-linked C-disaccharides using a carbon-Ferrier reaction

被引：17
|
作者：
Gemmell, N [1 ]
Meo, P [1 ]
Osborn, HMI [1 ]
机构：
[1] Univ Reading, Sch Chem, Reading RG6 6AD, Berks, England
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 10期
关键词：
D O I：
10.1021/ol030023t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The synthesis of unsaturated beta-linked C-disaccharides by the Lewis acid-mediated reaction of 3-O-acetylated glycals with monosaccharide-derived alkenes is described. Deprotection and selective hydrogenation of an exocyclic carbon-carbon double, in the presence of an endocyclic double bond, for representative targets is also illustrated.
引用
收藏
页码：1649 / 1652
页数：4
相关论文
共 50 条
  • [1] STEREOSELECTIVE SYNTHESIS OF DIPYRANYL C-DISACCHARIDES
    SUTHERLIN, DP
    ARMSTRONG, RW
    TETRAHEDRON LETTERS, 1993, 34 (31) : 4897 - 4900
  • [2] STEREOSELECTIVE SYNTHESIS OF LINEAR C-DISACCHARIDES
    DALY, SM
    ARMSTRONG, RW
    TETRAHEDRON LETTERS, 1989, 30 (42) : 5713 - 5716
  • [3] Stereoselective synthesis of α-C-L-fucopyranosyl containing C-disaccharides
    Rekai, ED
    Rubinstenn, G
    Mallet, JM
    Sinay, P
    Muller, SN
    Giese, B
    SYNLETT, 1998, (08) : 831 - +
  • [4] Wittig reaction of glycosyl phosphonium salts:: a stereoselective route to C-disaccharides and C,O-trisaccharides
    Colinas, PA
    Ponzinibbio, A
    Lieberknecht, A
    Bravo, RD
    TETRAHEDRON LETTERS, 2003, 44 (43) : 7985 - 7988
  • [5] A SIMPLE ROUTE TO BETA-LINKED C-DISACCHARIDES
    MARTIN, OR
    WEN, L
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 29 - CARB
  • [6] Synthesis of C-disaccharides an unusual ring closure reaction
    Khan, Abu T.
    Sharma, Parijat
    Schmidt, Richard R.
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (09) : 1353 - 1367
  • [7] THE SYNTHESIS OF DIFLUOROMETHYLENE-LINKED C-GLYCOSIDES AND C-DISACCHARIDES
    HERPIN, TF
    MOTHERWELL, WB
    TOZER, MJ
    TETRAHEDRON-ASYMMETRY, 1994, 5 (11) : 2269 - 2282
  • [8] The carbon-Ferrier rearrangement: an approach towards the synthesis of C-glycosides
    Ansari, Alafia Ali
    Lahiri, Rima
    Vankar, Yashwant D.
    ARKIVOC, 2013, : 316 - 362
  • [9] Approach to C-disaccharides using dithiane chemistry.
    Norris, P
    McCartney, JL
    Cicchillo, RM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U161 - U161
  • [10] Synthesis of C-glycosides and C-disaccharides using Mukaiyama aldol reaction in aqueous media
    Zeitouni, Jennifer
    Norsikian, Stephanie
    Merlet, Denis
    Lubineau, Andre
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) : 1662 - 1670
12345