(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R,19R)-5',7,9,13-tetramethyl-16-[[1-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]tetrazol-5-yl]methylamino]spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-18,19-diol | 1432631-66-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R,19R)-5',7,9,13-tetramethyl-16-[[1-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]tetrazol-5-yl]methylamino]spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-18,19-diol
• CAS: 1432631-66-7
• 化学式: C₅₆H₈₇N₅O₆
• 分子量: 926.337
• InChiKey: AXGFIUKJOJKLCS-BIPINFEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  67
• 可旋转键数：
  4
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (25R)-spirostan-22α-O-3β,5α,6β-triol 在 4-二甲氨基吡啶 、 sodium azide 、 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 170.25h， 生成 (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R,19R)-5',7,9,13-tetramethyl-16-[[1-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]tetrazol-5-yl]methylamino]spiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-18,19-diol
  参考文献：
  名称：

  Multicomponent Ligation of Steroids: Creating Diversity at the Linkage Moiety of Bis-spirostanic Conjugates by Ugi Reactions

  摘要：

  The diversity-oriented synthesis of novel bisspirostanic conjugates utilizing two different Up four-component reactions (Ugi-4CR) is described. Spirostanic steroids were functionalized with Ugi-reactive groups, that is, amines, isocyanides, and carboxylic acids, and next were subjected to multicomponent ligation approaches leading to bis-steroidal conjugates featuring pseudo-peptidic and hetero-cyclic linkage moieties. Both the classic Ugi-4CR and its hydrazoic acid variant were implemented, proving good efficiency for the ligation of isocyanosteroids to spirostanic acids and equatorial amines. Axially oriented amines showed poorer results, although model studies proved that chemical efficiency could be significantly improved while increasing reaction times. Overall, the method comprises the rapid generation of molecular diversity at the bis-steroid linkage moiety and, consequently, shows promise toward the production of combinatorial libraries of bis-spirostanes for biological screening.

  DOI：

  10.1021/co400028e