[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methyl 4-methylbenzenesulfonate | 328382-00-9

• 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: [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 328382-00-9
• 化学式: C₁₉H₃₂O₅SSi
• 分子量: 400.612
• InChiKey: LVXIGEHOCYRZOO-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methyl 4-methylbenzenesulfonate 在 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (2'R,3'S)-(3'-allyloxytetrahydropyran-2'-yl)acetonitrile
  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 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methyl 4-methylbenzenesulfonate
  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

文献信息

• Synthetic Studies on Ciguatoxin—Synthesis of H–I–J Ring System
  作者：Tong-Zhu Liu、Jian-Min Li、Minoru Isobe

  DOI：10.1016/s0040-4020(00)00865-6

  日期：2000.12

  Synthesis of a tricyclic ring system corresponding to H–I–J rings of ciguatoxin was stereoselectively achieved in 13 steps from a sugar derivative as a model study directed toward the total synthesis of ciguatoxin.

  作为模型研究的一部分，从糖衍生物的立体定向选择性合成西葫芦毒素的H–I–J环的三环系统是在13个步骤中完成的，该模型研究涉及雪茄毒素的全部合成。