From cyclic polyenes to carbohydrates:: synthesis of the hexose sugar β-allose and its 2C-branched homologue from cyclooctatetraene

被引:14
|
作者
Mehta, G [1 ]
Pallavi, K [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
D O I
10.1016/j.tetlet.2004.03.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In an unconventional but interesting synthetic enterprise, the commercially available hydrocarbon cyclooctatetraene (COT) has been elaborated to the rare hexose sugar (DL)-beta-allose and its 2C-branched analogue. The synthetic sequence delineated here is notable for its high regio- and stereoselectivity and is flexible enough to enable access to polyoxygenated systems, hexose sugars, and their siblings from a cyclic polyene precursor. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3865 / 3867
页数:3
相关论文
共 50 条
  • [1] CYCLIC POLYOLEFINS .2. SYNTHESIS OF CYCLOOCTATETRAENE FROM CHLOROPRENE
    COPE, AC
    BAILEY, WJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (07) : 2305 - 2309
  • [2] ADDITION OF PSEUDOHALOGENS TO UNSATURATED CARBOHYDRATES .3. SYNTHESIS OF 3-DEOXY-3-C-NITROMETHYL-D-ALLOSE, A BRANCHED-CHAIN NITRO SUGAR
    SZAREK, WA
    JEWELL, JS
    SZCZEREK, I
    JONES, JKN
    CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (23): : 4473 - &
  • [3] Internally Protected Amino Sugar Equivalents from Enantiopure 1,2-Oxazines: Synthesis of Variably Configured Carbohydrates with C-Branched Amino Sugar Units
    Pfrengle, Fabian
    Reissig, Hans-Ulrich
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (39) : 11915 - 11925
  • [4] Divergent synthesis of 2-C-branched pyranosides and oxepines from 1,2-gem-dibromocyclopropyl carbohydrates
    Moore, Peter W.
    Schuster, Julia K.
    Hewitt, Russell J.
    Stone, M. Rhia L.
    Teesdale-Spittle, Paul H.
    Harvey, Joanne E.
    TETRAHEDRON, 2014, 70 (39) : 7032 - 7043
  • [5] Synthesis of 1C-Aryl/Alkyl 2C-Branched Sugar-Fused Isochroman Derivatives by Sequential Prins and Friedel-Crafts Cyclizations on a Perlin Aldehyde Derived Substrate
    Rajasekaran, Parasuraman
    Mallikharjunarao, Yakkala
    Vankar, Yashwant D.
    SYNLETT, 2017, 28 (11) : 1346 - 1352
  • [6] DENOVO HIGHLY STEREOCONTROLLED SYNTHESIS OF 2,6-DIDEOXY-C-3-BRANCHED CARBOHYDRATES BY USE OF 2,6-ANHYDRO-2-THIO SUGAR - L-CLADINOSE AND ITS C-3 EPIMER
    TOSHIMA, K
    YOSHIDA, T
    MUKAIYAMA, S
    TATSUTA, K
    TETRAHEDRON LETTERS, 1991, 32 (33) : 4139 - 4142
  • [7] Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)
    Tian, Guang-Zong
    Hu, Jing
    Zhang, Heng-Xi
    Rademacher, Christoph
    Zou, Xiao-Peng
    Zheng, Hong-Ning
    Xu, Fei
    Wang, Xiao-Li
    Linker, Torsten
    Yin, Jian
    SCIENTIFIC REPORTS, 2018, 8
  • [8] Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)
    Guang-Zong Tian
    Jing Hu
    Heng-Xi Zhang
    Christoph Rademacher
    Xiao-Peng Zou
    Hong-Ning Zheng
    Fei Xu
    Xiao-Li Wang
    Torsten Linker
    Jian Yin
    Scientific Reports, 8
  • [9] N-Halosuccinimide/AgNO3-Efficient Reagent Systems for One-Step Synthesis of 2-Haloglycals from Glycals: Application in the Synthesis of 2C-Branched Sugars via Heck Coupling Reactions
    Dharuman, Suresh
    Vankar, Yashwant D.
    ORGANIC LETTERS, 2014, 16 (04) : 1172 - 1175
  • [10] Carbon-branched carbohydrate chirons: synthesis of C-3 and C-4-branched sugar lactones derived from D-erythronolactone
    Jenkinson, Sarah F.
    Booth, K. Victoria
    Estevez Reino, Amalia M.
    Horne, Graeme
    Estevez, Ramon J.
    Fleet, George W. J.
    TETRAHEDRON-ASYMMETRY, 2009, 20 (20) : 2357 - 2367