2-[(1S,2R,3aS,4aS,5S,5'R,6S,8aS,8bR)-1,5',8a-trimethyl-6-[(1R)-1-methyl-2-oxocyclohex-3-en-1-yl]spiro[3a,4,4a,5,6,7,8,8b-octahydro-1H-indeno[2,1-b]furan-2,2'-oxane]-5-yl]acetic acid | 325125-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(1S,2R,3aS,4aS,5S,5'R,6S,8aS,8bR)-1,5',8a-trimethyl-6-[(1R)-1-methyl-2-oxocyclohex-3-en-1-yl]spiro[3a,4,4a,5,6,7,8,8b-octahydro-1H-indeno[2,1-b]furan-2,2'-oxane]-5-yl]acetic acid
• CAS: 325125-66-4
• 化学式: C₂₇H₄₀O₅
• 分子量: 444.612
• InChiKey: DLKVBDKHQUBOEE-KETAVNOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1S,2R,3aS,4aS,5S,5'R,6S,8aS,8bR)-1,5',8a-trimethyl-6-[(1R)-1-methyl-2-oxocyclohex-3-en-1-yl]spiro[3a,4,4a,5,6,7,8,8b-octahydro-1H-indeno[2,1-b]furan-2,2'-oxane]-5-yl]acetic acid 在 palladium on activated charcoal 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (25R)-5,6-seco-A-homo-5(10)-oxa-5-oxo-spirostan-6-oic acid
  参考文献：
  名称：

  Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates

  摘要：

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.050
• 作为产物：
  描述：

  5A-羟基拉肖皂苷元 在 吡啶 、 jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2-[(1S,2R,3aS,4aS,5S,5'R,6S,8aS,8bR)-1,5',8a-trimethyl-6-[(1R)-1-methyl-2-oxocyclohex-3-en-1-yl]spiro[3a,4,4a,5,6,7,8,8b-octahydro-1H-indeno[2,1-b]furan-2,2'-oxane]-5-yl]acetic acid
  参考文献：
  名称：

  Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates

  摘要：

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.050

文献信息

• Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates
  作者：Daniel G. Rivera、Orlando Pando、Francisco Coll

  DOI：10.1016/j.tet.2006.06.050

  日期：2006.8

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.