Catalytic, stereoselective glycosylation -: Spiroketalization of 3,4,5-tri-O-benzyl-β-D-fructopyranose generating DI-D-fructopyranose-1,2′:2,1′-dianhydride

被引:3
|
作者
Kaji, Eisuke [1 ]
Saiga, Reiko [1 ]
Kurimoto, Emiko [1 ]
Nishino, Takashi [1 ]
机构
[1] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 1088641, Japan
关键词
D O I
10.3987/COM-06-S(O)50
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-D-Fructopyranose beta-D-fructopyranose-1,2':2,1'-dianhydride has been stereoselectively synthesized by tandem catalytic glycosylation-spiroketalization of 3,4,5-tri-O-benzyl-beta-D-fructo- pyranose. Of the several protic acid catalysts which exist, 0.3 molar equivalent trifluoromethane sulfonic acid in toluene was found to be most effective to afford the dianhydride in good yield.
引用
收藏
页码:385 / +
页数:10
相关论文
共 50 条
  • [1] DIHETEROLEVULOSAN IV-DI-BETA-D-FRUCTOPYRANOSE 1,2',2,1'-DIANHYDRIDE
    KANTERS, JA
    SCHOUTEN, A
    KROON, J
    MATHLOUTHI, M
    VANDERMAAS, JH
    LUTZ, B
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 : 1934 - 1937
  • [2] SYNTHESIS OF 1,2-ANHYDRO-3,4,5-TRI-O-BENZYL-BETA-D-FRUCTOPYRANOSE
    CAMPBELL, MM
    HEFFERNAN, GD
    LEWIS, T
    CARBOHYDRATE RESEARCH, 1994, 251 : 243 - 250
  • [3] STEREOSELECTIVE SYNTHESIS OF DI-BETA-D-FRUCTOPYRANOSE 1,2'/2,1'-DIANHYDRIDE, A SPIRODIOXANYL PSEUDODISACCHARIDE WITH METAL CATION COMPLEXING PROPERTIES
    FERNANDEZ, JMG
    SCHNELLE, RR
    DEFAYE, J
    TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 307 - 312
  • [4] Selective ruthenium-catalyzed oxidation of 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose and other alcohols with NaOCl
    Gonsalvi, L
    Arends, IWCE
    Sheldon, RA
    ORGANIC LETTERS, 2002, 4 (10) : 1659 - 1661
  • [5] 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose as chiral auxiliaries in Michael and aldol addition reactions
    Pinheiro, S
    Pedraza, SF
    Peralta, MA
    Carvalho, EM
    Farias, FMC
    Ferreira, VF
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (06) : 901 - 913
  • [6] STRUCTURE OF 3,4,5-TRI-O-ACETYL-1-DEOXY-1-[(2,2-DIMETHOXYCARBONYLVINYLAMINO]-BETA-D-FRUCTOPYRANOSE
    DIANEZ, MJ
    LOPEZCASTRO, A
    MARQUEZ, R
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 : 558 - 560
  • [7] Synthesis and X-ray structures of sulfate esters of fructose and its isopropylidene derivatives.: Part 1:: 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 1-sulfate and 4,5-O-isopropylidene-β-D-fructopyranose 1-sulfate
    Popek, T
    Lis, T
    CARBOHYDRATE RESEARCH, 2002, 337 (09) : 787 - 801
  • [8] Structure and 29Si NMR spectroscopy of chiral tri- and tetra-alkoxysilanes.: Observation of restricted rotation of 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose
    Madsen, J
    Clausen, RP
    Hazell, RG
    Jacobsen, HJ
    Bols, M
    Perry, CC
    ACTA CHEMICA SCANDINAVICA, 1998, 52 (09): : 1165 - 1170
  • [9] O2,O3:O4,O5-bis(phenylboranediyl)-β-D-fructopyranose acetone solvate
    Draffin, SP
    Duggan, PJ
    Fallon, GD
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1520 - O1522
  • [10] Acyl chloride/DABCO-promoted acetal migration of 1,2:4,5-di-O-isopropylidene-D-fructopyranose
    Meng, Xiang-Bao
    Li, Yun-Feng
    Li, Zhong-Jun
    CARBOHYDRATE RESEARCH, 2007, 342 (08) : 1101 - 1104