O-β-(6-O-galloyl)-glucopyranoside | 34781-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-β-(6-O-galloyl)-glucopyranoside
• 英文别名: β-D-glucose 6-O-gallate；1-O-galloyl-β-D-glucose；6-O-galloyl-β-D-glucose；6-O-galloyl-D-glucopyranoside；6-O-galloyl-D-glucopyranose；6-O-galloyl-glucose；6-O-galloyl-beta-D-glucose；[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 34781-46-9
• 化学式: C₁₃H₁₆O₁₀
• 分子量: 332.264
• InChiKey: VGVDLJNNDOFWKT-JEUROIALSA-N

物化性质

• 沸点：
  703.2±60.0 °C(Predicted)
• 密度：
  1.804±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 18.83h， 生成 O-β-(6-O-galloyl)-glucopyranoside
  参考文献：
  名称：

  Synthesis of gallotannins

  摘要：

  As a contribution to the synthesis of gallotannins, four O-galloyl-D-glucoses (3-O-, 6-O-, 3,6-di-O-, 3,4,6-tri-O-galloyl-D-glucose) have been prepared by the reaction of tri-O-benzylgalloyl chloride and partially protected glucose derivatives (1,2-O-, and 1,2:5,6-di-O-isopropylidene-alpha -D-glucofuranose), followed successively by catalytic debenzylation (Pd-C) and controlled acid hydrolysis. Their structures were established from their behavior on TLC and from their H-1 and C-13 NMR spectra. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00236-1

文献信息

• New oligomeric proanthocyanidins from Alhagi pseudalhagi
  作者：D. F. Alimova、Z. A. Kuliev、S. Z. Nishanbaev、A. D. Vdovin、N. D. Abdullaev、S. F. Aripova

  DOI：10.1007/s10600-010-9615-4

  日期：2010.7

  Two new oligomeric proanthocyanidin glucosides were isolated from the aerial part and roots of Alhagi pseudalhagi. Their structures and relative configurations were elucidated as 7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ galloyl-(+)catechin-(4α-8)-(+)-catechin-(4α-8)-(–)-epigallocatechin and 7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ galloyl-(+)-catechin-[(4α-8)-(+)-catechin]3-(4α-8)-(–)-epigallocatechin-3-O-gallate.

  从草木樨状黄芪的地上部分和根部中分离出两种新的寡聚原花青素葡萄糖苷。它们的结构和相对构型被阐明为7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ 没食子酰基-(+)-儿茶素-(4α-8)-(+)-儿茶素-(4α-8)-(–)-表儿茶素和7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ 没食子酰基-(+)-儿茶素-[(4α-8)-(+)-儿茶素]3-(4α-8)-(–)-表儿茶素-3-O-没食子酸盐。
• New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from Platanus orientalis trunk bark
  作者：S. Z. Nishanbaev、Z. A. Kuliev、N. K. Khidyrova、A. D. Vdovin、N. D. Abdullaev、Kh. M. Shakhidoyatov、O. A. Aripov

  DOI：10.1007/s10600-010-9616-3

  日期：2010.7

  Two new oligomeric proanthocyanidin glycosides were isolated from trunk bark of Platanus orientalis. Their structures and relative configurations were found to be 7-O-β-D-Glcp-(–)-epicatechin-(4β-8)-(–)-epicatechin(4β-8)-(–)-epicatechin-3-O-gallate (platanoside-A) and 7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ galloyl-(+)-catechin-3-O-gallate(4α-8)-(–)-epicatechin-3-O-gallate-(4β-8)-(–)-epicatechin-3-O-gallate-(4β-8)-5-O-β-D-Glcp-(–)epicatechin-3-O-gallate (platanoside-B).

  从桔梗树皮中分离出两种新的低聚原花青素苷。它们的结构和相对构型分别为 7-O-β-D-Glcp-(-)-epicatechin-(4β-8)-(-)-epicatechin(4β-8)-(-)-epicatechin-3-O-gallate (platanoside-A) 和 7-O-β-D-Glc$ \textp}}\xrightarrow6}$$ galloyl-(+)-catechin-3-O-gallate(4α-8)-(-)-epicatechin-3-O-gallate-(4β-8)-(-)-epicatechin-3-O-gallate-(4β-8)-5-O-β-D-Glcp-(-)epicatechin-3-O-gallate (platanoside-B)。