(3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(p-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone | 91312-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(p-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone
• 英文别名: (3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(para-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone；(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(p-tolylsulfonyloxymethyl)tetrahydropyran-2-one；(4R,6S)-4-tert-butyldimethylsilyloxy-6-(p-tosyloxymethyl)tetrahydropyran-2-one；(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(p-toluenesulphonyloxymethyl)tetrahydropyran-2-one；(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(p-toluenesulfonyloxymethyl)tetrahydropyran-2-one；[(2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 91312-59-3
• 化学式: C₁₉H₃₀O₆SSi
• 分子量: 414.595
• InChiKey: ZRMCTCWVSHERPN-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-hydroxy-5-(tert-butyl-dimethylsilyloxy)-(1S,3R,5R)-cyclohexyl acetate 在 吡啶 、 甲醇 、 sodium acetate 、 potassium carbonate 、 对甲苯磺酸 、 magnesium bromide ethyl etherate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(p-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone
  参考文献：
  名称：

  Efficient Synthesis of Optically Pure (4R,6S)-4-(tert-Butyldimethylsilyloxy)- 6-(hydroxymethyl)tetrahydropyran-2-one and Its Enantiomer

  摘要：

  DOI：

  10.1021/jo015774s

文献信息

• Synthesis of the Chiral Side Chain of Statins – Lactone versus Lactol Pathway
  作者：Vitali I. Tararov、Natalia Andrushko、Vasyl Andrushko、Gerd König、Anke Spannenberg、Armin Börner

  DOI：10.1002/ejoc.200600849

  日期：2006.12

  pivotal intermediates for the synthesis of pharmacologically important statins. Remarkably, up to now no proof for this assumption can be derived from the literature. Our study revealed that only silyl-type protecting groups can be successfully employed for 3-O-protection of initial ethyl (3R,5S)-3-hydroxy-5,6-(isopropylidenedioxy)hexanoate (1). After cyclization, hydroxy lactone 3b was transformed into

  4-O-受保护的 (4R,6S)-4-羟基-6-(羟基甲基)四氢吡喃-2-酮 (3) 衍生自对映异构纯 (3R,5S)-3-羟基-5,6-(异亚丙基二氧基)己酸酯(2) 通常被认为是合成具有药理意义的他汀类药物的关键中间体。值得注意的是，到目前为止，无法从文献中得出关于这一假设的证据。我们的研究表明，只有甲硅烷基类型的保护基团才能成功用于初始 (3R,5S)-3-羟基-5,6-(异亚丙基二氧基)己酸乙酯 (1) 的 3-O-保护。环化后，羟基内酯 3b 转化为甲苯磺酸酯 5b，依次转化为碘化物 6b。后者被转化为膦酸酯9b。通过甲苯磺酸盐 5b 的 X 射线结构分析证实了中间体的所有立体化学归属和非对映异构纯度。出奇，甲苯磺酸盐 5b 和碘化物 6b 都不能转化为相应的腈 7b，腈 7b 是制备阿托伐他汀的关键中间体。膦酸酯 9b 和醛 4b 是最接近氟伐他汀和瑞舒伐他汀内酯的中间体。不幸的是，膦酸酯
• Synthetic and biological studies of compactin and related compounds. 2. Synthesis of the lactone moiety of compactin
  作者：Terry Rosen、Michael J. Taschner、Clayton H. Heathcock

  DOI：10.1021/jo00195a023

  日期：1984.10
• Bakers' yeast oxidation of methyl para-tolylsuifide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents
  作者：Jenny Tang、Ian Brackenridge、Stanley M. Roberts、Jean Beecher、Andrew J. Willetts

  DOI：10.1016/0040-4020(95)00819-t

  日期：1995.11

  The use of (R)-methyl para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomerically pure beta-silyloxy-delta-lactone. The chiral sulfoxide used in the synthesis was obtained via a straightforward biooxidation of methyl paratolylsulfide using bakers' yeast (Saccharomyces cerevisiae NCYC 73). The biotransformation involves the use of whole cells and affords the sulfoxide in good yield and with high stereoselectivity.
• Beecher, Jean; Brackenridge, Ian; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1641 - 1644
  作者：Beecher, Jean、Brackenridge, Ian、Roberts, Stanley M.、Tang, Jenny、Willetts, Andrew J.

  DOI：——

  日期：——
• [DE] VERFAHREN ZUR HERSTELLUNG VON STATINEN<br/>[EN] METHOD FOR THE PRODUCTION OF STATINS<br/>[FR] PROCEDE DE FABRICATION DE STATINES
  申请人：RATIOPHARM GMBH

  公开号：WO2005047276A3

  公开（公告）日：2005-10-06