methyl (8R)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-(trifluoromethylsulfonyloxy)oct-5-ynoate | 188255-11-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl (8R)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-(trifluoromethylsulfonyloxy)oct-5-ynoate
• CAS: 188255-11-0
• 化学式: C₁₇H₂₃F₃O₈S
• 分子量: 444.426
• InChiKey: BGEVSZPIBCPUNI-QVHKTLOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (8R)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-(trifluoromethylsulfonyloxy)oct-5-ynoate 在 四丁基碘化铵 、 mercury dichloride 、 mercury(II) oxide 、 zinc(II) chloride 作用下， 以 吡啶 、 水 、 丙酮 、 苯 为溶剂， 反应 35.0h， 生成 (9S,11R)-8-Iodo-12-oxo-9,11-bis-triethylsilanyloxy-dodec-5-ynoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2α methyl ester by a biomimetic process

  摘要：

  The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF(2 alpha) methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF(2 alpha), an useful tool for biological studies. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00100-7
• 作为产物：
  描述：

  (3aR,5S,6aR)-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl (8R)-8-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-8-(trifluoromethylsulfonyloxy)oct-5-ynoate
  参考文献：
  名称：

  Total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2α methyl ester by a biomimetic process

  摘要：

  The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF(2 alpha) methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF(2 alpha), an useful tool for biological studies. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00100-7

文献信息

• Total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF2α methyl ester by a biomimetic process
  作者：Alexandre Guy、Thierry Durand、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1016/s0040-4039(97)00100-7

  日期：1997.3

  The first total synthesis of 15(RS)-5,6-dehydro-8-epi-PGF(2 alpha) methyl ester 1 with high stereoselectivity and good yield, is described using D-glucose as starting material. This novel isoprostane is a potent precursor of labelled (deutered and/or tritiated) 8-epi-PGF(2 alpha), an useful tool for biological studies. (C) 1997 Published by Elsevier Science Ltd.