[(3aS,4R,6aR)-2,2,4,5,5-pentadeuterio-3a,6a-dihydro-3H-furo[2,3-b]furan-4-yl] (4S,5R)-5-deuterio-5-[[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]methyl]-2,2-dimethyl-4-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-3-carboxylate | 1443118-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: [(3aS,4R,6aR)-2,2,4,5,5-pentadeuterio-3a,6a-dihydro-3H-furo[2,3-b]furan-4-yl] (4S,5R)-5-deuterio-5-[[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]methyl]-2,2-dimethyl-4-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-3-carboxylate
• CAS: 1443118-38-4
• 化学式: C₃₈H₄₆N₂O₁₀S
• 分子量: 739.722
• InChiKey: VVNSOVIECVHDSP-HPZKSFGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  51
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,6aR)-2,2,4,5,5-pentadeuterio-3a,6a-dihydro-3H-furo[2,3-b]furan-4-yl] (4S,5R)-5-deuterio-5-[[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]methyl]-2,2-dimethyl-4-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 [(3aS,4R,6aR)-2,2,4,5,5-pentadeuterio-3a,6a-dihydro-3H-furo[2,3-b]furan-4-yl] (4S,5R)-5-deuterio-5-[[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]methyl]-4-[(4-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs

  摘要：

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.001
• 作为产物：
  描述：

  Dideuterium benzo[d][1,3]dioxol 在 三氧化硫 N,N-二甲基甲酰胺络合物 、 草酰氯 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 22.83h， 生成 [(3aS,4R,6aR)-2,2,4,5,5-pentadeuterio-3a,6a-dihydro-3H-furo[2,3-b]furan-4-yl] (4S,5R)-5-deuterio-5-[[(2,2-dideuterio-1,3-benzodioxol-5-yl)sulfonyl-[1,1,2,3,3,3-hexadeuterio-2-(trideuteriomethyl)propyl]amino]methyl]-2,2-dimethyl-4-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs

  摘要：

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.001

文献信息

• Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs
  作者：Emile J. Velthuisen、Todd M. Baughman、Brian A. Johns、David P. Temelkoff、Jason G. Weatherhead

  DOI：10.1016/j.ejmech.2013.02.001

  日期：2013.5

  Several highly deuterated analogs of the HIV-1 protease inhibitor brecanavir have been prepared to study the effect of deuterium upon metabolic stability. The sites for deuterium incorporation were initially chosen to maximize the potential for a kinetic isotope effect; locations where C-H bond breaking is the rate limiting step. The analogs have been profiled in both in vitro and in vivo pharmacokinetic studies and the result will be described herein. (C) 2013 Elsevier Masson SAS. All rights reserved.