(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-,3α,22,23-trihydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-methylboronate | 1244967-01-8

• 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,22,23-trihydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-methylboronate
• CAS: 1244967-01-8
• 化学式: C₃₅H₆₃BO₆Si
• 分子量: 618.778
• InChiKey: BSTCUAYYGUAVBV-HHQQOJNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-,3α,22,23-trihydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-methylboronate 在 草酸氯化物 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-22,23-dihydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-3,6-dione 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,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan-6-one 22,23-methylboronate 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以82%的产率得到(22R,23R,24R)-2α-(dimethyl-tert-butylsilyl)-,3α,22,23-trihydroxy-24-methyl-B-homo-7-oxa-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

文献信息

• Synthesis of fatty acyl derivatives of 24-epibrassinolide
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Dmitrii V. Tsavlovskii

  DOI：10.1016/j.jsbmb.2013.01.016

  日期：2013.9

  myristinic or lauric acid chlorides gave the corresponding esters. The hydrolysis of 22,23-methylboronates was performed after their transformation into 2-hydroxy-1,3,2-dioxaborolanes using a cation exchange column with DOWEX 50WX8 in NH4(+) form. Hydrogenolysis of the benzyl ethers catalyzed by palladium yielded the target compounds. This article is part of a Special Issue entitled "Synthesis and biological

  表油菜素内酯的许多脂肪酸（棕榈酸，肉豆蔻酸和月桂酸）酯（3α-和3β-异构体）均已制备为代谢研究的参考化合物。先后以环状22,23-甲基硼酸酯然后以2α-苄基醚的形式依次对表油菜素内酯的四个羟基中的三个进行选择性保护。通过连续的氧化还原反应或通过3α-甲磺酸酯的亲核取代实现C-3羟基的α，β转化。用棕榈酸，肉豆蔻酸或月桂酸氯化物处理3α-和3β-醇，得到相应的酯。使用具有NH4（+）形式的DOWEX 50WX8的阳离子交换柱，将22,23-甲基硼酸酯水解为2-羟基-1,3,2-二氧杂硼烷后，进行水解。钯催化的苄基醚的氢解产生目标化合物。本文是名为“类固醇衍生物作为抑制剂的合成和生物学测试”的特刊的一部分。