2-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-ethanol | 385841-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-ethanol
• 英文别名: 2-[(2S,3R,4R)-4-[tert-butyl(diphenyl)silyl]oxy-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-yl]ethanol
• CAS: 385841-97-4
• 化学式: C₂₇H₃₈O₅Si
• 分子量: 470.681
• InChiKey: ZMVPKDWANOWNTJ-JBXUNAHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-ethanol 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 3-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-propionitrile
  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：

  [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到2-[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-yl]-ethanol
  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

文献信息

• AL-12182, a novel 11-oxa prostaglandin analog with topical ocular hypotensive activity in the monkey
  作者：Robert D Selliah、Mark R Hellberg、Najam A Sharif、Marsha A McLaughlin、Gary W Williams、Daniel A Scott、David Earnest、Karen S Haggard、W Dennis Dean、Pete Delgado、Michael S Gaines、Raymond E Conrow、Peter G Klimko

  DOI：10.1016/j.bmcl.2004.06.037

  日期：2004.9

  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.