(3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-pyridin-2-ylazetidin-2-one | 512186-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-pyridin-2-ylazetidin-2-one
• CAS: 512186-57-1
• 化学式: C₁₅H₂₄N₂O₂Si
• 分子量: 292.453
• InChiKey: PCAHUDPLVNIZAV-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-pyridin-2-ylazetidin-2-one 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 生成 [(2R,4S,6S,7R,10R,13S,14R,15S,16S,18S)-13-acetyloxy-16-hydroxy-18-[(2R,3S)-2-hydroxy-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyridin-2-ylpropanoyl]oxy-7,19,20,20-tetramethyl-4-(morpholin-4-ylmethyl)-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 3

  摘要：

  We synthesized novel water-soluble and orally active taxane analogues, 7-deoxy-9beta-dihydro-9,10-O-acetal taxanes. Cytotoxicities of the synthetic compounds were greater than those of paclitaxel and docetaxel, especially against resistant cancer cell lines expressing P-glycoprotein. In addition, some compounds showed potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00891-0
• 作为产物：
  描述：

  methyl 2-(tert-butyldimethylsilyloxy)propanoate 、 (E)-1-pyridin-2-yl-N-trimethylsilylmethanimine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-pyridin-2-ylazetidin-2-one
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 3

  摘要：

  We synthesized novel water-soluble and orally active taxane analogues, 7-deoxy-9beta-dihydro-9,10-O-acetal taxanes. Cytotoxicities of the synthetic compounds were greater than those of paclitaxel and docetaxel, especially against resistant cancer cell lines expressing P-glycoprotein. In addition, some compounds showed potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00891-0

文献信息

• New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 3
  作者：Yasuyuki Takeda、Toshiharu Yoshino、Kouichi Uoto、Jun Chiba、Takashi Ishiyama、Michio Iwahana、Takeshi Jimbo、Noriko Tanaka、Hirofumi Terasawa、Tsunehiko Soga

  DOI：10.1016/s0960-894x(02)00891-0

  日期：2003.1

  We synthesized novel water-soluble and orally active taxane analogues, 7-deoxy-9beta-dihydro-9,10-O-acetal taxanes. Cytotoxicities of the synthetic compounds were greater than those of paclitaxel and docetaxel, especially against resistant cancer cell lines expressing P-glycoprotein. In addition, some compounds showed potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration. (C) 2002 Elsevier Science Ltd. All rights reserved.