Imino glycals in synthesis:: Preparation of novel deoxymannojirimycin analogues

被引：0
|
作者：
Désiré, J [1 ]
Shipman, M [1 ]
机构：
[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
来源：
SYNLETT | 2001年 / 08期
关键词：
carbohydrates; piperidines; stereoselective synthesis; imino glycals; glycosidases;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of imino glucal 2 from tetra-O-benzyl-D-glucopyranose in 7 steps is described. This imino sugar building block is converted into conformationally constrained deoxymannojirimycin analogue (+)-9 by means of a stereocontrolled cyclopropanation followed by a two step deprotection sequence. Regioselective fission of the cyclopropane ring prior to deprotection provides access to related analogue (+)-11.
引用
收藏
页码：1332 / 1334
页数：3
相关论文
共 50 条
  • [1] Chemistry of imino glycals:: Preparation and application to the synthesis of (+)-fagomine
    Désiré, J
    Dransfield, PJ
    Gore, PM
    Shipman, M
    SYNLETT, 2001, (08) : 1329 - 1331
  • [2] Preparation and reactivity of imino glycals: stereocontrolled, divergent approach to imino sugars
    Dransfield, PJ
    Gore, PM
    Prokes, I
    Shipman, M
    Slawin, AMZ
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (15) : 2723 - 2733
  • [3] PREPARATION OF NOVEL MONOSACCHARIDE AND DISACCHARIDE GLYCALS FOR THE SYNTHESIS OF OLIGODEOXY OLIGOSACCHARIDES
    THIEM, J
    OSSOWSKI, P
    SCHWENTNER, J
    CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03): : 955 - 969
  • [4] Divergent approach to imino sugar C-glycosides using imino glycals:: application to the stereocontrolled synthesis of (+)-deoxoprosophylline
    Dransfield, PJ
    Gore, PM
    Shipman, M
    Slawin, AMZ
    CHEMICAL COMMUNICATIONS, 2002, (02) : 150 - 151
  • [5] Povarov reactions of exo-glycals: preparation of C-linked, quinoline analogues
    Dobbelaar, Peter H.
    Marzabadi, Cecilia H.
    TETRAHEDRON, 2011, 67 (48) : 9273 - 9282
  • [6] Glycomimetics: A versatile de novo synthesis of beta-1-C-aryl-deoxymannojirimycin analogues
    Johnson, CR
    Johns, BA
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17): : 6046 - 6050
  • [7] Preparation of novel hexythiazox analogues
    Novak, L
    Hornyanszky, G
    Rohaly, J
    Kolonits, P
    Szantay, C
    PESTICIDE SCIENCE, 1997, 49 (01): : 85 - 89
  • [8] Synthesis of Dihydroxymethyl Dihydroxypyrrolidines and Steviamine Analogues from C-2 Formyl Glycals
    Ansari, Alafia A.
    Vankar, Yashwant D.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9383 - 9395
  • [9] Imino Glycals via Ruthenium-Catalyzed RCM and Isomerization
    Schmidt, Bernd
    Hauke, Sylvia
    Muehlenberg, Nino
    SYNTHESIS-STUTTGART, 2014, 46 (12): : 1648 - 1658
  • [10] Synthesis of poly(imino imino ketone) (PIIK) and preparation of heat resistant PIIK foam
    Chang, Guanjun
    Yang, Li
    Yang, Junxiao
    Huang, Yawen
    Cao, Ke
    Zhang, Lin
    Lin, Runxiong
    POLYMER, 2013, 54 (18) : 5043 - 5049
12345