(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene | 130912-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene
• 英文别名: (2S,3S,4R,5R,6R)-2-benzyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 130912-39-9
• 化学式: C₃₄H₃₆O₅
• 分子量: 524.657
• InChiKey: LYVOSLSKZMWQGK-IWJWPENGSA-N

物化性质

• 沸点：
  665.9±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 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：

  溴甲苯 在 sodium hydroxide 、 四(三苯基膦)钯 、 dimethyl sulfide borane 、 双氧水 作用下， 以 甲苯 为溶剂， 生成 (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene
  参考文献：
  名称：

  通过钯催化的三丁基锡烷基糖基与有机卤化物的偶联反应形成C-糖苷

  摘要：

  1-（三丁基锡烷基）-D-葡糖与不饱和卤化物的钯催化偶联反应提供了相应的1- C-烷基化的葡糖，这是1,3-二溴苯对称或不对称二C-糖基化的有效方法。

  DOI：

  10.1039/c39900001191

文献信息

• Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-d-glucals with organic halides
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1016/s0008-6215(00)90552-4

  日期：1992.4

  1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst. This mild reaction is specially useful for the preparation of 1-C-aryl-D-glucals and compatible with unprotected hydroxy groups or hindered aromatic bromides. It has been shown that the resulting 1-C-aryl(alkyl)-D-glucals

  由相应的1-苯基磺酰基-D-葡萄糖制备的1-三丁基锡烷基-D-葡萄糖在钯（0）催化剂的存在下有效地偶联到各种有机卤化物上。这种温和的反应对于制备1-C-芳基-D-葡萄糖特别有用，并且与未保护的羟基或受阻的芳香族溴化物相容。已经表明，所得的1-C-芳基（烷基）-D-葡萄糖适用于烯醇醚基团的进一步合成操作，包括立体选择性氢化，硼氢化-氧化或环氧化。所有形成的化合物都是由试剂对葡糖衍生物的α-面的攻击所致。反应扩展到1，3-，1，4-二-和1,3,5-三溴苯，导致相应的对称的二-（三）-C-葡萄糖基苯。最后，顺序的二-C-葡萄糖基化为1
• 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.
• Formation of C-glycosides by a palladium-catalysed coupling reaction of tributylstannyl glycals with organic halides
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1039/c39900001191

  日期：——

  The palladium-catalysed coupling reaction of 1-(tributylstannyl)-D-glucals with unsaturated halides furnishes the corresponding 1-C-alkylated glucals, an efficient procedure for a symmetric or dis-symmetric di-C-glycosidation of 1,3-dibromobenzene.

  1-（三丁基锡烷基）-D-葡糖与不饱和卤化物的钯催化偶联反应提供了相应的1- C-烷基化的葡糖，这是1,3-二溴苯对称或不对称二C-糖基化的有效方法。