1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene | 368878-02-8

• 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: 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene
• 英文别名: 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-(hydroxymethyl)androst-5-ene；[(1S,3R,8S,9S,10R,13S,14S,17S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]methanol
• CAS: 368878-02-8
• 化学式: C₃₂H₆₀O₃Si₂
• 分子量: 548.998
• InChiKey: LSODJWZIAFWBST-KTSQDRBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.95
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 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)-17β-(hydroxymethyl)androst-5-ene 在 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 生成 3-[[(1S,2R,5S,6S,9R,10R,11S,13R,15S)-11,13-bis[[tert-butyl(dimethyl)silyl]oxy]-6,10-dimethyl-17,19-dioxo-18-phenyl-16,18,20-triazahexacyclo[13.5.2.01,9.02,6.010,15.016,20]docos-21-en-5-yl]methoxy]-N,N-dimethylpropanamide
  参考文献：
  名称：

  Synthesis of 21-nor-22-oxa-1α,25-dihydroxyvitamin D3 derivatives in quest of a drug with low calcemic activity

  摘要：

  Two 21-nor-22-oxa- 1alpha,25-dihydroxyvitamin D-3 derivatives have been synthesized in quest of a drug with lower calcemic activity than Maxacalcitol, 22-oxa-1alpha,25-dihydroxyvitamin D-3, being used as antihyperparathyroidism and antipsoriatic drug. Of two 21-nor products obtained, the product carrying one carbon elongated side chain with diethylcarbinol moiety has been found to exhibit comparable differentiation-inducing activity to Maxacalcitol with much lower exhibition of calcemic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.160
• 作为产物：
  描述：

  1α,3β-bis<(tert-butyldimethylsilyl)oxy>androst-5-en-17-one 在 9-borabicyclo[3.3.1]nonane dimer 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androst-5-ene
  参考文献：
  名称：

  Synthesis of 21-nor-22-oxa-1α,25-dihydroxyvitamin D3 derivatives in quest of a drug with low calcemic activity

  摘要：

  Two 21-nor-22-oxa- 1alpha,25-dihydroxyvitamin D-3 derivatives have been synthesized in quest of a drug with lower calcemic activity than Maxacalcitol, 22-oxa-1alpha,25-dihydroxyvitamin D-3, being used as antihyperparathyroidism and antipsoriatic drug. Of two 21-nor products obtained, the product carrying one carbon elongated side chain with diethylcarbinol moiety has been found to exhibit comparable differentiation-inducing activity to Maxacalcitol with much lower exhibition of calcemic activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.160

文献信息

• Vitamin d derivatives
  申请人：——

  公开号：US20030195176A1

  公开（公告）日：2003-10-16

  The object of the present invention is to provide a vitamin D derivative exhibiting excellent physiological activity as medicines, in particular as therapeutic agents for skin disease including psoriasis, and having decreased hypercalcemic activity. The present invention provides vitamin D derivatives represented by the general Formula ( 1 ): 1 wherein in Formula ( 1 ), X is oxygen or sulfur; R 1 is hydrogen or Formula ( 2 ) 2 R 2 is hydrogen or alkyl; R 3 and R 4 are hydrogen or alkyl or R 3 and R 4 together form a double bond between the 16 - and 17 -positions; R 5 is hydrogen or -OR 13 in which R 13 is hydrogen or a protecting group; and R 6 is hydrogen or a protecting group.

  本发明的目的是提供一种表现出优异生理活性的维生素D衍生物作为药物，特别是作为治疗包括牛皮癣在内的皮肤疾病的药剂，并且具有降低的高钙血症活性。 本发明提供了由通式（1）表示的维生素D衍生物： 其中在通式（1）中，X为氧或硫； R1为氢或通式（2）； R2为氢或烷基； R3和R4为氢或烷基，或者R3和R4共同形成16-和17-位置之间的双键； R5为氢或-OR13，其中R13为氢或保护基；以及 R6为氢或保护基。
• Vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07074777B2

  公开（公告）日：2006-07-11

  The object of the present invention is to provide a vitamin D derivative exhibiting excellent physiological activity as medicines, in particular as therapeutic agents for skin disease including psoriasis, and having decreased hypercalcemic activity. The present invention provides vitamin D derivatives represented by the general Formula (1): wherein in Formula (1), X is oxygen or sulfur; R1 is hydrogen or Formula (2) R2 is hydrogen or alkyl; R3 and R4 are hydrogen or alkyl or R3 and R4 together form a double bond between the 16- and 17-positions; R5 is hydrogen or —OR13 in which R13 is hydrogen or a protecting group; and R6 is hydrogen or a protecting group.

  本发明的目的是提供一种维生素D衍生物，作为药物表现出优异的生理活性，特别是作为治疗皮肤疾病，包括银屑病的治疗剂，并具有降低的高钙血症活性。本发明提供了由通式（1）表示的维生素D衍生物：其中在式（1）中，X是氧或硫；R1是氢或式（2）；R2是氢或烷基；R3和R4是氢或烷基，或R3和R4共同形成16位和17位之间的双键；R5是氢或—OR13，其中R13是氢或保护基；R6是氢或保护基。
• Synthesis of 21-nor-22-oxa-1α,25-dihydroxyvitamin D3 derivatives in quest of a drug with low calcemic activity
  作者：Hitoshi Shimizu、Kazuki Shimizu、Yasushi Uchiyama、Atsuko Sugita、Tetsuhiro Mikami、Tsuyoshi Yamauchi、Masahiro Kato、Kazumi Morikawa

  DOI：10.1016/j.tetlet.2004.08.160

  日期：2004.10

  Two 21-nor-22-oxa- 1alpha,25-dihydroxyvitamin D-3 derivatives have been synthesized in quest of a drug with lower calcemic activity than Maxacalcitol, 22-oxa-1alpha,25-dihydroxyvitamin D-3, being used as antihyperparathyroidism and antipsoriatic drug. Of two 21-nor products obtained, the product carrying one carbon elongated side chain with diethylcarbinol moiety has been found to exhibit comparable differentiation-inducing activity to Maxacalcitol with much lower exhibition of calcemic activity. (C) 2004 Elsevier Ltd. All rights reserved.