S-tert-butyl (2R)-2-[(1R,7aR)-7a-methyl-5-oxo-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate | 203392-60-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-tert-butyl (2R)-2-[(1R,7aR)-7a-methyl-5-oxo-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate
• 英文别名: S-tert-butyl (2R)-2-[(1R,7aR)-7a-methyl-5-oxo-4-phenylsulfanyl-2,3,6,7-tetrahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate
• CAS: 203392-60-3
• 化学式: C₃₁H₄₄O₄S₂
• 分子量: 544.82
• InChiKey: AJOWMRPZLYIQJW-TVGMPGEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-tert-butyl (2R)-2-[(1R,7aR)-7a-methyl-5-oxo-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate 在 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Toluene-4-sulfonic acid (R)-2-((1R,7aR)-5-hydroxy-7a-methyl-4-phenylsulfanyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl)-4-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 24,25-dihydroxy vitamin D3 northern portion from (S)-3-hydroxy-2,2-dimethylcyclohexane-1-one. Remote asymmetric induction in an acid-catalysed conjugate addition

  摘要：

  Enantioselective synthesis of building blocks, 2 and 16, for 24,25-dihydroxy- and 25-hydroxy vitamin D synthesis, respectively, from easily accessible optically active hydroxy ketone 5, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10647-5
• 作为产物：
  描述：

  S-tert-butyl 4-[(3S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate 在 氢氧化钾 、 triphenylmethylium hexachloroantimonate(V) 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 S-tert-butyl (2R)-2-[(1R,7aR)-7a-methyl-5-oxo-4-phenylthio-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl]-4-[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]butanethioate
  参考文献：
  名称：

  Enantioselective synthesis of 24,25-dihydroxy vitamin D3 northern portion from (S)-3-hydroxy-2,2-dimethylcyclohexane-1-one. Remote asymmetric induction in an acid-catalysed conjugate addition

  摘要：

  Enantioselective synthesis of building blocks, 2 and 16, for 24,25-dihydroxy- and 25-hydroxy vitamin D synthesis, respectively, from easily accessible optically active hydroxy ketone 5, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10647-5

文献信息

• Enantioselective Total Synthesis of atrans-Hydrindane Rings/Side-Chain Building-Block of Vitamin D− Asymmetric Induction in an Acid-Catalyzed Conjugate-Addition Reaction
  作者：Evgueni Gorobets、Viatcheslav Stepanenko、Jerzy Wicha

  DOI：10.1002/ejoc.200300611

  日期：2004.2

  For the enantioselective total synthesis of 1α,25-dihydroxyvitamin D3 (3), we have developed an enantioselective approach to the “northern” portion building-block 8, starting from the optically active hexanoic acid derivative 44, 2-methylcyclopent-2-en-1-one (10) and 1-(phenylthio)but-3-en-2-one (9). The steric course of the addition reaction of homochiral (S)-ketene acetals 28, 40, 44 and 58 with

  对于 1α,25-二羟基维生素 D3 (3) 的对映选择性全合成，我们开发了一种对“北部”部分构建块 8 的对映选择性方法，从光学活性己酸衍生物 44, 2-methylcyclopent-2-en 开始-1-一 (10) 和 1-(苯硫基)but-3-en-2-one (9)。检查了同手性 (S)-烯酮缩醛 28、40、44 和 58 与 10 的加成反应的空间过程。我们发现，在 28、44 和 40 的情况下，反应以高的简单和诱导（面部）非对映选择性发生。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)