1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene | 210219-14-0

• 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: 1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene
• 英文别名: 1alpha,3beta-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene；(1R)-1-[(1S,3R,9S,10R,13S,14S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-10,13-dimethyl-2,3,4,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol
• CAS: 210219-14-0
• 化学式: C₃₃H₅₈O₃Si₂
• 分子量: 558.993
• InChiKey: KCERYUSEDXNNHR-QJIPWPKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene 在 lithium aluminium tetrahydride 、 四丙基高钌酸铵 、 15-冠醚-5 、 4 A molecular sieve 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-(2-hydroxy-2-methylpropoxy)pregna-5,7,16-triene
  参考文献：
  名称：

  Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1α,25-(OH)2D3 analogs

  摘要：

  A series of 16-en-22-oxa-derivatives of vitamin D-3 based on the structure of maxacalcitol (2) were prepared. Maxacalcitol is currently used topically for the treatment of psoriasis and is recognized as the most successful antedrug of natural vitamin D-3 because it retains the original antiproliferative activity of calcitriol without increased calcemic activity. We introduced 16-olefinic functionality to accelerate the oxidative metabolism of the drug in liver, presumed to be essential for the reduction of calcemic activity, and modified the side-chain moiety by placing the 22-oxygen on the more labile allylic carbon center. Novel 22-oxa analogs (7a-i), carrying either the 24-alkynyl bond or 24-hydroxy functionality in addition to the 16-double bond were synthesized and their pharmacokinetics were evaluated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.034
• 作为产物：
  描述：

  (1α,3β)-1,3-bis((tert-butyl(dimethyl)silyl)oxy)pregna-5,7,16-trien-20-one 、 cerium(III) chloride heptahydrate 在 sodium borohydrid 作用下， 以 甲醇 为溶剂， 以73%的产率得到1α,3β-bis(tert-butyldimethylsilyloxy)-20(R)-hydroxypregna-5,7,16-triene
  参考文献：
  名称：

  US6184398

  摘要：

  公开号：

文献信息

• Vitamin d derivatives
  申请人：——

  公开号：US20040019023A1

  公开（公告）日：2004-01-29

  The object of the present invention is to provide vitamin D derivatives that have excellent physiological activities as medicines, particularly as therapeutic agents for skin diseases such as psoriasis, and that have a reduced hypercalcemic effect. The present invention provides a vitamin D derivative of Formula (1): 1 wherein X represents an oxygen atom or a sulfur atom; m represents a number of 1 to 3; R 1 and R 2 each represent a hydrogen atom or an alkyl group; R 4 and R 5 each represent a hydrogen atom or a hydroxyl group, etc.; R 3 represents —YR 8 , etc.; R 6 represents a hydrogen atom, etc.; and R 7 represents a hydrogen atom, etc.

  本发明的目的是提供作为药物的维生素D衍生物，特别是作为治疗银屑病等皮肤疾病的治疗剂，并且具有减少高钙血症作用的维生素D衍生物。 本发明提供了化学式（1）的维生素D衍生物： 1 其中 X代表氧原子或硫原子； m代表1至3的数字； R 1 和R 2 分别代表氢原子或烷基； R 4 和R 5 分别代表氢原子或羟基等； R 3 代表—YR 8 等； R 6 代表氢原子等；以及 R 7 代表氢原子等。
• 16-ENE-VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020193616A1

  公开（公告）日：2002-12-19

  The compound of the formula (24): 1 wherein R 9 R 10 may be the same or different and each represent a hydrogen atom or a protecting group.

  化学式（24）的化合物：其中R9和R10可以相同或不同，且均表示氢原子或保护基。
• 16-ene-vitamin D derivatives
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020032340A1

  公开（公告）日：2002-03-14

  A compound having the formula (4): wherein 1 X is oxygen or sulfur, R 9 and R 10 are each a hydrogen or a protecting group, and R 11 is an aliphatic hydrocarbon, a —COR 12 group where R 12 is alkyl, aryl or alkoxy, or a group of formula 2 wherein R 5 and R 6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  一个化合物的化学式为(4)，其中1X是氧或硫，R9和R10分别是氢或保护基团，R11是脂肪烃、—COR12基团（其中R12是烷基、芳基或烷氧基）或化学式2中的基团（其中R5和R6分别是氢或羟基，m为1到4，n为0-2）。
• Intermediates for preparation of 16-ene-vitamin D derivatives
  申请人：Chugei Seiyaku Kabushiki Kaisha

  公开号：US06433200B1

  公开（公告）日：2002-08-13

  Intermediates for the preparation of a vitamin D derivative have the following formulas: wherein R9 and R10 may be the same or different and each represents a hydrogen atom or a protecting group, and in Formula (5) the conjugated double bond may be protected by a protecting group.

  制备维生素D衍生物的中间体具有以下公式：其中R9和R10可以相同也可以不同，分别代表氢原子或保护基，在公式（5）中，共轭双键可以由保护基保护。
• 16-ENE-vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06326503B1

  公开（公告）日：2001-12-04

  A compound having the formula (4): wherein X is oxygen or sulfur, R9 and R10 are each a hydrogen or a protecting group, and R11 is an aliphatic hydrocarbon, a —COR12 group where R12 is alkyl, aryl or alkoxy, or a group of formula wherein R5 and R6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  化合物的化学式为（4）：其中X为氧或硫，R9和R10分别为氢或保护基，R11为脂肪烃、-COR12基团，其中R12为烷基、芳基或烷氧基，或者为式中的基团，其中R5和R6分别为氢或羟基，m为1至4，n为0-2。