(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3α-methanesulfonyl-22,23-dihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate | 1244966-95-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3α-methanesulfonyl-22,23-dihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate
• 英文别名: [(2R,3S,5S,8S,9S,10R,13S,14S,17R)-2-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-17-[(1S)-1-[(4R,5R)-2-methyl-5-[(2R)-3-methylbutan-2-yl]-1,3,2-dioxaborolan-4-yl]ethyl]-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] methanesulfonate
• CAS: 1244966-95-7
• 化学式: C₃₆H₆₅BO₇SSi
• 分子量: 680.87
• InChiKey: ATGHEURPAKQAHO-KFFYKYJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3α-methanesulfonyl-22,23-dihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate 在 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以50%的产率得到(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3β,22,23-trihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate
  参考文献：
  名称：

  Preparation and synthetic application of partially protected brassinosteroids

  摘要：

  Preparation of partially protected brassinosteroids is achieved through the reaction of the source material (24-epicastasterone and 24-epibrassinolide) with diol-specific reagents (2,2-dimethoxypropane and methylboronic acid). The obtained products were shown to be useful synthetic intermediates for further preparation of minor representatives of this class of natural phytohormones (such as 3 24, diepicastasterone and 3-dehydro-24-epibrassinolide). (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.09.010
• 作为产物：
  描述：

  (22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3α,22,23-trihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate 、 甲基磺酰氯 在 吡啶 作用下， 以87%的产率得到(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-3α-methanesulfonyl-22,23-dihydroxy-24-methyl-5α-cholestan-6-one 22,23-methylboronate
  参考文献：
  名称：

  Preparation and synthetic application of partially protected brassinosteroids

  摘要：

  Preparation of partially protected brassinosteroids is achieved through the reaction of the source material (24-epicastasterone and 24-epibrassinolide) with diol-specific reagents (2,2-dimethoxypropane and methylboronic acid). The obtained products were shown to be useful synthetic intermediates for further preparation of minor representatives of this class of natural phytohormones (such as 3 24, diepicastasterone and 3-dehydro-24-epibrassinolide). (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.09.010