26,27-二去甲基-1,3-(叔-丁基二甲基硅烷基)(5Z)-骨化三醇24-羧酸甲酯 | 145372-43-6

• 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
• 中文名称: 26,27-二去甲基-1,3-(叔-丁基二甲基硅烷基)(5Z)-骨化三醇24-羧酸甲酯
• 中文别名: 26,27-二甲基-1,3-（叔丁基二甲基甲硅烷基）（5Z）-骨化三醇24-羧酸甲酯
• 英文名称: 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether
• 英文别名: 1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D₃ tert-butyldimethylsilyl ether；26,27-Didesmethyl-1,3-(tert-butyldimethylsilyl) (5Z)-Calcitriol 24-Carboxylic Acid Methyl Ester；methyl (5R)-5-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]hexanoate
• CAS: 145372-43-6
• 化学式: C₃₈H₆₈O₄Si₂
• 分子量: 645.127
• InChiKey: OWGWSEUEDPLMHW-MUWHYZOISA-N

物化性质

• 沸点：
  608.3±55.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.17
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  26,27-二去甲基-1,3-(叔-丁基二甲基硅烷基)(5Z)-骨化三醇24-羧酸甲酯 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 34.0h， 生成 骨化三醇
  参考文献：
  名称：

  Ultrasonically induced conjugate addition of iodides to electron-deficient olefins and its application to the synthesis of side-chain analogs of the hormone 1.alpha.,25-dihydroxyvitamin D3

  摘要：

  DOI：

  10.1021/jo00053a023
• 作为产物：
  描述：

  1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether 在 喹啉 、 Lindlar's catalyst 、 氢气 作用下， 以 异辛烷 、 正己烷 为溶剂， 反应 13.0h， 生成 26,27-二去甲基-1,3-(叔-丁基二甲基硅烷基)(5Z)-骨化三醇24-羧酸甲酯
  参考文献：
  名称：

  Ultrasonically induced conjugate addition of iodides to electron-deficient olefins and its application to the synthesis of side-chain analogs of the hormone 1.alpha.,25-dihydroxyvitamin D3

  摘要：

  DOI：

  10.1021/jo00053a023

文献信息

• An Expeditious Route to 1α,25-Dihydroxyvitamin D₃and Its Analogues by an Aqueous Tandem Palladium-Catalyzed A-Ring Closure and Suzuki Coupling to the C/D Unit
  作者：Pranjal Gogoi、Rita Sigüeiro、Silvina Eduardo、Antonio Mouriño

  DOI：10.1002/chem.200902972

  日期：2010.2.1

  mild, general, and highly stereoselective Pd0‐catalyzed cascade to the triene system of the hormone 1α,25‐dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol–triflate (lower fragment) followed in situ by Suzuki–Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0‐catalyzed coupling) in equimolar amounts

  每日维生素：有轻度，一般和高度立体选择性的Pd 0催化与1α，25-二羟基维生素D 3和6种代表性类似物的三烯系统级联。在质子化条件下等摩尔量的烯醇-三氟甲磺酸分子的分子内环化（下片段），然后是铃木-宫浦（Suzuki-Miyaura）与烯基硼酸酯（上片段，也可通过Pd 0催化偶联有效制备）原位合成用于生物测试的少量新维生素D类似物（请参阅计划）。
• Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol
  作者：Michał Chodyński、Wanda Wojciechowska、Sebastian J. Halkes、Jan-Paul van de Velde、Andrzej Kutner

  DOI：10.1016/s0039-128x(97)00040-8

  日期：1997.7

  A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a,24b-dihomo-1,25-dihydroxycholecalciferol (1) are described. Novel C-23a,C-24-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent compound 1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane 12 or Wittig reagent 15 for the preparation of compound 1 and analog 4, respectively. Introduction of 24aE double bond bond results in a selective, 1000-fold increase in the binding affinity of analog 4 for the vitamin D receptor, compared to the affinity of 1, whereas the affinity of 4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged. (C) 1997 by Elsevier Science Inc.