(2S,3R,4R,5S,6S)-6-Allyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 594847-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6S)-6-Allyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 594847-57-1
• 化学式: C₂₂H₄₄O₆Si₂
• 分子量: 460.759
• InChiKey: ZJDRDPHFMNFPDC-OYSTVDSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6S)-6-Allyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 咪唑 、 四丁基氟化铵 、 水 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[3-[4-[(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-11-yl]-N-methylanilino]propyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  An Evaluation of a C-Glucuronide as a liver targeting group: conjugate of a glucocorticoid antagonist

  摘要：

  A beta-C-glucuronide conjugate of the glucocorticoid receptor antagonist, Mifepristone 1, was prepared which maintained binding affinity, had modest in vitro activity, and was metabolically more stable than the parent. Pharmacokinetic studies suggest that the conjugate is recognized by the liver like O-glucuronides and may undergo a portion of the enterohepatic recirculation loop. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00431-1
• 作为产物：
  描述：

  methyl (3,4-di-O-tert-butyldimethylsilyl-D-glucuronate)glycal 在 二甲基二环氧乙烷 、 三正丁基锡三氟基磺酸盐 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4R,5S,6S)-6-Allyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  An Evaluation of a C-Glucuronide as a liver targeting group: conjugate of a glucocorticoid antagonist

  摘要：

  A beta-C-glucuronide conjugate of the glucocorticoid receptor antagonist, Mifepristone 1, was prepared which maintained binding affinity, had modest in vitro activity, and was metabolically more stable than the parent. Pharmacokinetic studies suggest that the conjugate is recognized by the liver like O-glucuronides and may undergo a portion of the enterohepatic recirculation loop. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00431-1