3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionaldehyde | 748816-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionaldehyde
• CAS: 748816-50-4
• 化学式: C₂₈H₃₈O₅Si
• 分子量: 482.692
• InChiKey: QVMSPQMSAHPTFU-SSUZURRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionaldehyde 在 sodium hexamethyldisilazane 、 高碘酸 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 生成 (Z)-7-{(2R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-[(E)-4-(3-chloro-phenoxy)-3-oxo-but-1-enyl]-tetrahydro-furan-3-yl}-hept-4-enoic acid isopropyl ester
  参考文献：
  名称：

  AL-12182, a novel 11-oxa prostaglandin analog with topical ocular hypotensive activity in the monkey

  摘要：

  A series of 11-oxa prostaglandin analogs was evaluated for FP receptor binding and activation. Several compounds having aryloxy-terminated lower chains were found to be potent agonists. Topical ocular dosing of AL-12182, the isopropyl ester prodrug of the potent agonist 13, lowered intraocular pressure in the monkey by 40% accompanied by minimal conjunctival hyperemia in the rabbit. AL-12182 was synthesized on multigram scale starting with D-sorbitol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.037
• 作为产物：
  描述：

  3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionitrile 在 二异丁基氢化铝 、 溶剂黄146 作用下， 以 正己烷 、 甲苯 为溶剂， 以94%的产率得到3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionaldehyde
  参考文献：
  名称：

  AL-12182, a novel 11-oxa prostaglandin analog with topical ocular hypotensive activity in the monkey

  摘要：

  A series of 11-oxa prostaglandin analogs was evaluated for FP receptor binding and activation. Several compounds having aryloxy-terminated lower chains were found to be potent agonists. Topical ocular dosing of AL-12182, the isopropyl ester prodrug of the potent agonist 13, lowered intraocular pressure in the monkey by 40% accompanied by minimal conjunctival hyperemia in the rabbit. AL-12182 was synthesized on multigram scale starting with D-sorbitol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.037