(1R,3R)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5,5-ethylenedithio-2-methylenecyclohexane | 1155975-20-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (1R,3R)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5,5-ethylenedithio-2-methylenecyclohexane
• 英文别名: tert-butyl-[[(7R,9R)-7-[tert-butyl(dimethyl)silyl]oxy-8-methylidene-1,4-dithiaspiro[4.5]decan-9-yl]oxy]-dimethylsilane
• CAS: 1155975-20-4
• 化学式: C₂₁H₄₂O₂S₂Si₂
• 分子量: 446.866
• InChiKey: UEXDQPZTXQBGLW-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,3R)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5,5-ethylenedithio-2-methylenecyclohexane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以55%的产率得到(1R,3R)-3-[(tert-butyldimethylsilyl)oxy]-5,5-ethylenedithio-2-methylenecyclohexanol
  参考文献：
  名称：

  19-Nor-Vitamin D Analogs with 1,2-Dihydrofuran Ring

  摘要：

  描述了具有额外二氢呋喃环连接类似物A环的1α-氧和碳-2的19-去维生素D类似物，以及其药用。这些化合物在体外和体内表现出选择性活性，使它们成为治疗自身免疫疾病、某些类型的癌症、继发性甲状旁腺功能亢进症、银屑病或其他皮肤疾病的治疗药物。

  公开号：

  US20100009944A1
• 作为产物：
  描述：

  (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione 在 正丁基锂 、 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.5h， 生成 (1R,3R)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5,5-ethylenedithio-2-methylenecyclohexane
  参考文献：
  名称：

  19-Nor-Vitamin D Analogs with 1,2-Dihydrofuran Ring

  摘要：

  描述了具有额外二氢呋喃环连接类似物A环的1α-氧和碳-2的19-去维生素D类似物，以及其药用。这些化合物在体外和体内表现出选择性活性，使它们成为治疗自身免疫疾病、某些类型的癌症、继发性甲状旁腺功能亢进症、银屑病或其他皮肤疾病的治疗药物。

  公开号：

  US20100009944A1

文献信息

• 19-NOR-VITAMIN D ANALOGS WITH 3,2-DIHYDROFURAN RING
  申请人：DeLuca Hector F.

  公开号：US20100009945A1

  公开（公告）日：2010-01-14

  19-nor-vitamin D analogs having an additional dihydrofuran ring connecting the 3β-oxygen and carbon-2 of the A-ring of the analog, and pharmaceutical uses therefore, are described. These compounds exhibit selective in vitro and in vivo activities, making them therapeutic agents for the treatment or prophylaxis of autoimmune diseases, some types of cancers, metabolic bone diseases, osteomalacia, osteopenia, secondary hyperparathyroidism, psoriasis, or other skin diseases.

  描述了具有额外二氢呋喃环连接模拟物A环的3β-氧和碳-2的19-去维生素D类似物，并因此具有药用价值。这些化合物在体外和体内表现出选择性活性，使它们成为治疗或预防自身免疫疾病、某些类型的癌症、代谢性骨病、软骨软化症、骨质疏松症、继发性甲状旁腺功能亢进症、银屑病或其他皮肤疾病的治疗剂。
• New 1α,25-Dihydroxy-19-norvitamin D₃ Compounds Constrained in a Single A-Ring Conformation: Synthesis of the Analogues by Ring-Closing Metathesis Route and Their Biological Evaluation
  作者：Agnieszka Glebocka、Katarzyna Sokolowska、Rafal R. Sicinski、Lori A. Plum、Hector F. DeLuca

  DOI：10.1021/jm9001583

  日期：2009.6.11

  Vitamin D compounds possessing A rings prohibited from flipping to the alternative chair form (i.e., analogues 2 and 26) were synthesized. The bicyclic fragment 22 consisting of the fused cyclohexane and dihydropyran rings was constructed via the ring-closing metathesis route. Also, a homologous synthon 23 with an attached dihydropyran ring was successfully synthesized using this strategy. The carbonyl deprotection in 22 yielded cyclohexanone 5 that was subjected to Julia coupling with the anion of the phenylthiazoline sulfone 25. In the resulting isomeric 19-norvitamins 2 and 26, their A rings can exist only in the alpha- and beta-conformation. The analogue 26 was 300 times more active in binding to the vitamin D receptor protein, 30 times more effective in causing HL-60 differentiation, and 10 times more active in transcription. These results confirm that the beta-chair form of the vitamin D ring A is necessary for the binding to the receptor.
• 19-Nor-Vitamin D Analogs with 1,2-Dihydrofuran Ring
  申请人：DeLuca Hector F.

  公开号：US20100009944A1

  公开（公告）日：2010-01-14

  19-nor-vitamin D analogs having an additional dihydrofuran ring connecting the 1α-oxygen and carbon-2 of the A-ring of the analog, and pharmaceutical uses therefore, are described. These compounds exhibit selective in vitro and in vivo activities, making them therapeutic agents for the treatment or prophylaxis of autoimmune diseases, some types of cancers, secondary hyperparathyroidism, psoriasis, or other skin diseases.

  描述了具有额外二氢呋喃环连接类似物A环的1α-氧和碳-2的19-去维生素D类似物，以及其药用。这些化合物在体外和体内表现出选择性活性，使它们成为治疗自身免疫疾病、某些类型的癌症、继发性甲状旁腺功能亢进症、银屑病或其他皮肤疾病的治疗药物。