(Z)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester | 863288-56-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester
• 英文别名: methyl (Z)-3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]prop-2-enoate
• CAS: 863288-56-6
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: DCJJESZUJZLSDK-BWFAQCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(Z)-3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]prop-2-en-1-ol
  参考文献：
  名称：

  The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.126
• 作为产物：
  描述：

  (2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3S)-disubstituted tetrahydropyranes with diverse functional groups using known methodologies. In addition to the tert-butyl dimethyl silyl group, other common protecting groups for hydroxyl groups such as allyl, acetate, and benzoate were used to obtain appropriate derivatives. Pure compounds were evaluated in vitro against HL60 human leukemia cells and MCF7 human breast cancer cells. From the growth inhibition data a structure-activity relationship was obtained. Overall the results point to the relevant role of the tert-butyl dimethyl silyl group in the modulation of cytotoxic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.126