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<(1R)-endo>-(+)-2-Bornyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside

中文名称
——
中文别名
——
英文名称
<(1R)-endo>-(+)-2-Bornyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside
英文别名
((1R)-endo)-(+)-2-Bornyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside;[(2R,3R,4S,5R,6R)-3,4,5-tris[(4-bromobenzoyl)oxy]-6-[[(1R,2S,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]oxy]oxan-2-yl]methyl 4-bromobenzoate
<(1R)-endo>-(+)-2-Bornyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside化学式
CAS
——
化学式
C44H40Br4O10
mdl
——
分子量
1048.41
InChiKey
KCKASXXPCRJXCS-BKBNKTNFSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    12.1
  • 重原子数:
    58
  • 可旋转键数:
    15
  • 环数:
    7.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    124
  • 氢给体数:
    0
  • 氢受体数:
    10

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    (+)-冰片2,3,4,6-Tetrakis-O-(p-bromobenzoyl)-α-D-glucopyranosyl bromidesilver trifluoromethanesulfonate1,1,3,3-四甲基脲 作用下, 以 二氯甲烷 为溶剂, 反应 0.5h, 以63%的产率得到<(1R)-endo>-(+)-2-Bornyl 2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranoside
    参考文献:
    名称:
    CD and 1H NMR Study of the Rotational Population Dependence of the Hydroxymethyl Group in .beta. Glucopyranosides on the Aglycon and Its Absolute Configuration
    摘要:
    The rotamer population around the C5-C6 bond of chiral and nonchiral alkyl P-D-glucopyranoside derivatives proved to be dependent on the structure of the aglycon; the population of the gg and gt rotamers decreased and increased, respectively, as the pK(a) of the aglycon increased, whereas the rs tg population remained almost constant. In addition, the rotamer populations correlate with the absolute configuration of the aglyconic carbons, namely, higher CD A values and smaller (3)J(H5,H6R) coupling constants are obtained for the (R)-alkyl glucopyranosides than for their (S)-alkyl glucopyranoside counterparts, as the result of increased and decreased gg and gt populations, respectively. The results show a clear relationship between the rotamer distributions and the stereoelectronic exo-anomeric effect. Asa consequence of these findings the absolute configuration of secondary alcohols can be determined, a single enantiomer being necessary for this purpose.
    DOI:
    10.1021/jo00113a038
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文献信息

  • CD and 1H NMR Study of the Rotational Population Dependence of the Hydroxymethyl Group in .beta. Glucopyranosides on the Aglycon and Its Absolute Configuration
    作者:Ezequiel Q. Morales、Juan I. Padron、Mar Trujillo、Jesus T. Vazquez
    DOI:10.1021/jo00113a038
    日期:1995.4
    The rotamer population around the C5-C6 bond of chiral and nonchiral alkyl P-D-glucopyranoside derivatives proved to be dependent on the structure of the aglycon; the population of the gg and gt rotamers decreased and increased, respectively, as the pK(a) of the aglycon increased, whereas the rs tg population remained almost constant. In addition, the rotamer populations correlate with the absolute configuration of the aglyconic carbons, namely, higher CD A values and smaller (3)J(H5,H6R) coupling constants are obtained for the (R)-alkyl glucopyranosides than for their (S)-alkyl glucopyranoside counterparts, as the result of increased and decreased gg and gt populations, respectively. The results show a clear relationship between the rotamer distributions and the stereoelectronic exo-anomeric effect. Asa consequence of these findings the absolute configuration of secondary alcohols can be determined, a single enantiomer being necessary for this purpose.
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