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
  • [21] SYNTHESIS OF GLYCOSYL AZIDES OR BENZOATES FROM CYCLIC SULFITES IN C-1,C-2
    GUILLER, A
    GAGNIEU, CH
    PACHECO, H
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (02) : 161 - 168
  • [22] EN-ROUTE TO THROMBOXANE COMPOUNDS FROM CARBOHYDRATES .2. HALOLACTONIZATION OF 4-C-BRANCHED ALKYL HEX-2-ENOPYRANOSIDES
    PELYVAS, IF
    LINDHORST, TK
    BATTA, G
    THIEM, J
    LIEBIGS ANNALEN DER CHEMIE, 1992, (01): : 33 - 37
  • [23] Synthesis of sedoheptulose from 2-C-(hydroxymethyl)-D-allose by molybdic acid-catalysed carbon-skeleton rearrangement
    Hricovíniová-Bíliková, Z
    Petrus, L
    CARBOHYDRATE RESEARCH, 1999, 320 (1-2) : 31 - 36
  • [24] REACTIONS AND SYNTHESIS OF A NOVEL NITRONE DERIVED FROM 2,5-ANHYDRO-D-ALLOSE, A NEW ENTRY INTO C-GLYCOSYL NUCLEOSIDES
    HEISE, GL
    HARMON, RE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 31 - CARB
  • [25] Synthesis of Oxepines and 2-Branched Pyranosides from a D-Glucal-Derived gem-Dibromo-1,2-cyclopropanated Sugar
    Hewitt, Russell J.
    Harvey, Joanne E.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03): : 955 - 958
  • [26] Application of sugar-containing biomass: one-step synthesis of 2-furylglyoxylic acid and its derivatives from a vitamin C precursor
    Chen, Jiao
    Zhu, Zhenhua
    Cai, Jiali
    Cao, Mengru
    Sha, Feng
    Tao, Sha
    Yang, Hao
    Gan, Haifeng
    Wu, Hongli
    Cao, Fei
    Zhao, Lili
    Ouyang, Pingkai
    GREEN CHEMISTRY, 2022, 24 (05) : 2000 - 2009
  • [27] Synthesis of C2-symmetrical cyclic guanidino-sugars from D-mannitol
    Gauzy, L
    Le Merrer, Y
    Depezay, JC
    SYNLETT, 1998, (04) : 402 - +
  • [28] DENOVO SYNTHESIS OF CARBOHYDRATES AND RELATED NATURAL-PRODUCTS .23. SYNTHESIS OF 2-DEOXY-DL-RIBO-HEXOSE AND 6-DEOXY-DL-TALOSE FROM MESO-DIVINYLGLYCOLS
    KUFNER, U
    SCHMIDT, RR
    LIEBIGS ANNALEN DER CHEMIE, 1986, (09): : 1610 - 1620
  • [29] UNSTABILIZED DIAZO DERIVATIVES FROM CARBOHYDRATES - APPLICATION TO THE SYNTHESIS OF 2-DEAMINO-TUNICAMINE AND PRODUCTS RELATED TO C-DISACCHARIDES
    SARABIAGARCIA, F
    LOPEZHERRERA, FJ
    GONZALEZ, MSP
    TETRAHEDRON, 1995, 51 (18) : 5491 - 5500
  • [30] SYNTHESIS OF 2-AMINO-2-DEOXY-D-ALLOSE 2-AMINO-2-DEOXY-D-ALTROSE AND 2-DEOXY-D-RIBO-HEXOSE FROM 3,4,5,6-TETRAACETOXY-D-RIBO-1-NITRO-1-HEXENE
    PERRY, MB
    FURDOVA, J
    CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1968, 46 (17): : 2859 - +