(8R,9S,10R,13S,14S,17S)-17-[1-[[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]triazol-4-yl]-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one | 1555636-04-8

• 分子结构分类: 有机化合物
• 英文名称: (8R,9S,10R,13S,14S,17S)-17-[1-[[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]triazol-4-yl]-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 1555636-04-8
• 化学式: C₃₆H₄₇N₃O₆
• 分子量: 617.786
• InChiKey: UBQJXDLMJZPBAE-HNPMQVQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  104.93
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 copper(l) iodide 、 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (8R,9S,10R,13S,14S,17S)-17-[1-[[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]triazol-4-yl]-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

  摘要：

  Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4 center dot 5H(2)O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, H-1 & C-13 NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.11.022