(1R,3R,7E,22E,24E)-24a-homo-19-nor-9,10-secoergosta-5,7,22,24-tetraen-1,3,25-triol | 1263286-76-5

• 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: (1R,3R,7E,22E,24E)-24a-homo-19-nor-9,10-secoergosta-5,7,22,24-tetraen-1,3,25-triol
• 英文别名: (1R,3R,7E,22E,24E)-24a,26,27-trihomo-19-nor-9,10-secoergosta-5,7,22,24-tetraeno-1,3,25-triol；(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,3E,5E)-7-ethyl-7-hydroxy-5-methylnona-3,5-dien-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol
• CAS: 1263286-76-5
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: NBGWUSUHGDZOAM-UAYYXJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (7E)-(1R,3R)-24-phenylsulfonyl-1,3-bis(tert-butyldimethylsililoxy)-9,10-seco-19,22,23-trinorchola-5,7-dien 在 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 5.75h， 生成 (1R,3R,7E,22E,24E)-24a-homo-19-nor-9,10-secoergosta-5,7,22,24-tetraen-1,3,25-triol
  参考文献：
  名称：

  Synthesis and crystallographic study of 1,25-dihydroxyergocalciferol analogs

  摘要：

  The hybrid analogs of 1,25-dihydroxyergocalciferol (PRI-5201 and PRI-5202) were synthesized as potential anticancer agents using a convergent strategy. The analogs were designed by combining a 19-nor modification of the A-ring with the homologated and rigidified ergocalciferol-like side-chain of the previously obtained analogs PRI-1906 and PRI-1907. The strategy also allowed the novel efficient synthesis of 19-nor-1,25-dihydroxyergocalciferol (paricalcitol, PRI-5100) and its (24R)-diastereomer (PRI-5101). The single crystal X-ray structures of the 19-nor analogs (PRI-5100 and PRI-5101) were solved and refined. The A-ring of both analogs adopts exclusively chair beta-conformation in the solid state. The side-chain of these analogs is coplanar with the CD-ring plane, while it is perpendicular in 1,25-dihydroxycholecalciferol. Crown Copyright (C) 2013 Published by Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.06.001

文献信息

• NEW SYNTHONES FOR PREPARATION OF 19-NOR VITAMIN D DERIVATIVES
  申请人：Chodynski Michal

  公开号：US20130006003A1

  公开（公告）日：2013-01-03

  The present invention discloses the synthone of Formula (I), wherein R 1 and R 2 are the same or different and represent independently hydrogen atom or hydroxyl protecting group, and its use for preparation of 19-nor vitamin D derivatives of general Formula (IV), wherein represents single or double bond, p represents an integer 0 to 3, R 1 and R 2 represent independently hydrogen atom or hydroxyl protecting group, R 3 represents hydrogen atom, CH 3 or hydroxyl group, R 4 , R 5 and R 6 represent independently hydrogen atom, C 1 -C 3 -alkyl or hydroxyl group or two of R 4 , R 5 and R 6 substituents altogether form cyclopropyl group, in particular for preparation of paricalcitol.

  本发明揭示了公式（I）的合成物，其中R1和R2相同或不同，分别独立表示氢原子或羟基保护基，以及其用于制备一般公式（IV）的19-去维生素D衍生物，其中表示单键或双键，p表示整数0至3，R1和R2分别表示氢原子或羟基保护基，R3表示氢原子、CH3或羟基，R4、R5和R6分别表示氢原子、C1-C3-烷基或羟基，或R4、R5和R6中的两个取代基共同形成环丙基，特别用于制备帕立卡钙。