(2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol | 909533-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol
• CAS: 909533-47-7
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: DHIRWYWNYOUQKC-PXTPFGJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol 、 乙酸酐 在 吡啶 作用下， 生成 [(2R,3R,4R,5S,6S)-3,5-diacetyloxy-6-benzyl-4-phenylmethoxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

  摘要：

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.060
• 作为产物：
  描述：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 (2S,3S,4R,5R,6R)-2-benzyl-6-(hydroxymethyl)-4-phenylmethoxyoxane-3,5-diol
  参考文献：
  名称：

  Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

  摘要：

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.060

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.
• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.