(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-13-(2-aminoethyl)-5',7,9,13-tetramethylspiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-16-one | 909879-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-13-(2-aminoethyl)-5',7,9,13-tetramethylspiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-16-one
• CAS: 909879-64-7
• 化学式: C₂₇H₄₃NO₄
• 分子量: 445.643
• InChiKey: NZGJZPJPTAHJID-BNQSYQKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-13-(2-aminoethyl)-5',7,9,13-tetramethylspiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-16-one 以 甲醇 为溶剂， 反应 7.0h， 生成 tert-butyl N-[(2S)-1-[[2-(tert-butylamino)-2-oxoethyl]-[2-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-5',7,9,13-tetramethyl-16-oxospiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-13-yl]ethyl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamate
  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：

  (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19R)-16-[tert-butyl(dimethyl)silyl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-ol 在 Lindlar's catalyst 吡啶 、 氢氧化钾 、 sodium azide 、 四丁基氟化铵 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 116.0h， 生成 (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,18R)-13-(2-aminoethyl)-5',7,9,13-tetramethylspiro[5,17-dioxapentacyclo[10.7.0.02,9.04,8.014,18]nonadecane-6,2'-oxane]-16-one
  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.