Methyl 2-O-β-D-glucopyranosyl-α-L-rhamnopyranoside

被引：2
|
作者：
Eriksson, L [1 ]
Stenutz, R
Widmalm, G
机构：
[1] Stockholm Univ, Div Struct Chem, SE-10691 Stockholm, Sweden
[2] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
来源：
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | 2002年 / 58卷 / 06期
关键词：
D O I：
10.1107/S0108270102005905
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The overall conformation of the title compound, C13H24O10, is described by the glycosidic torsion angles φH (H1g-C1g-O2r-C2r) and ψH (C1g-O2r-C2r-H2r), which have values of 13.6 and 16.1°, respectively. The former is significantly different from the value predicted by consideration of the exo-anomeric effect (φH ∼ 60°) and from that in solution (φH ∼ 50°), as determined previously by NMR spectroscopy. An intramolecular O3r-H⋯O2g hydrogen bond may help to stabilize the conformation in the solid state. The orientation of the hydroxymethyl group of the glucose residue is gauche-gauche, with a torsion angle ω (O5g-C5g-C6g-O6g) of -70.4 (4)°. Both pyranose rings are in their expected chair conformations, i.e. 4C1 for D-glucose and 1C4 for L-rhamnose.
引用
收藏
页码：O328 / O329
页数：2
相关论文
共 50 条
  • [1] Synthesis of di-O-glycosyl derivatives of methyl α-L-rhamnopyranoside
    Nifant'ev, N.E.
    Lipkind, G.M.
    Shashkov, A.S.
    Kochetkov, N.K.
    Carbohydrate Research, 1992, 223 : 109 - 128
  • [2] Methyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
    Hanna, K.
    Jonsson, M.
    Eriksson, Lars
    Widmalm, Göran
    Acta Crystallogr Sect C Cryst Struct Commun, 8 (o447-o449):
  • [3] Methyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
    Jonsson, K. Hanna M.
    Eriksson, Lars
    Widmalm, Goran
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2006, 62 : O447 - O449
  • [4] Delphinidin 3-O-(2-O-β-D-glucopyranosyl-α-L-arabinopyranoside):: A novel anthocyanin identified in Beluga black lentils
    Takeoka, GR
    Dao, LT
    Tamura, H
    Harden, LA
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (12) : 4932 - 4937
  • [5] Evaluation of the antioxidant potential of myricetin 3-O-α-L-rhamnopyranoside and myricetin 4′-O-α-L-rhamnopyranoside through a computational study
    Rodrigo A. Mendes
    Shawan K. C. Almeida
    Iuri N. Soares
    Cristina A. Barboza
    Renato G. Freitas
    Alex Brown
    Gabriel L. C. de Souza
    Journal of Molecular Modeling, 2019, 25
  • [6] Synthesis of potassium (2R)-2-O-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute
    Lourenco, Eva C.
    Maycock, Christopher D.
    Ventura, M. Rita
    CARBOHYDRATE RESEARCH, 2009, 344 (15) : 2073 - 2078
  • [7] Crystal structure of methyl α-L-rhamnopyranosyl-(1→2)-α-L-rhamnopyranoside monohydrate
    Eriksson, Lars
    Widmalm, Goran
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 854 - +
  • [8] Quantum chemical studies on the partial hydrogenolysis of methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside
    Mandi, Attila
    Komaromi, Istvan
    Borbas, Aniko
    Szikra, Dezso
    Nagy, Istvan P.
    Liptak, Andras
    Antus, Sandor
    TETRAHEDRON LETTERS, 2011, 52 (12) : 1256 - 1259
  • [9] A new cardenolide uzarigenin-3-O-β-D-xylopyranosyl (1→2)-α-L-rhamnopyranoside
    Yadava, RN
    Yadav, S
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 1999, 1 (04) : 245 - 249
  • [10] Antioxidant properties of 2-O-β-D-glucopyranosyl-L-ascorbic acid
    Takebayashi, Jun
    Yagi, Yasuyuki
    Ishii, Rie
    Abe, Shigeki
    Yamada, Kazuhiko
    Tai, Akihiro
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2008, 72 (06) : 1558 - 1563
12345