(2S,3R,4R,5S,6R)-2-Benzyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3,4-diol | 909533-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-2-Benzyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2S,3R,4R,5S,6R)-2-benzyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 909533-31-9
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: CVYOMFYWELCXRQ-XQDVFQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene 在 palladium on activated charcoal 氢气 作用下， 生成 (2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol 、 (2S,3R,4R,5S,6R)-2-Benzyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3,4-diol 、 (2S,3S,4R,5R,6R)-2-benzyl-4-phenylmethoxy-6-(phenylmethoxymethyl)oxane-3,5-diol 、 (2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-3-ol
  参考文献：
  名称：

  Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells

  摘要：

  A large series of alkyl C-glycosides was synthesized from D-glucal or D-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-galacto- or C-mannopyranosides, exhibited inhibitory concentrations (IC50 values) below 20 mu M, five of them in the range 4-8 mu M. Preliminary structure-activity relationships were established. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.079

文献信息

• Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells
  作者：Carlos A. Sanhueza、Carlos Mayato、María García-Chicano、Raquel Díaz-Peñate、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2006.05.079

  日期：2006.8

  A large series of alkyl C-glycosides was synthesized from D-glucal or D-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-galacto- or C-mannopyranosides, exhibited inhibitory concentrations (IC50 values) below 20 mu M, five of them in the range 4-8 mu M. Preliminary structure-activity relationships were established. (c) 2006 Elsevier Ltd. All rights reserved.