2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran | 96686-94-1

• 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: 2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran
• 英文别名: 2-[[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane
• CAS: 96686-94-1
• 化学式: C₃₂H₅₄O₂
• 分子量: 470.78
• InChiKey: JTBDYRSHSZVOOZ-CJTOWZGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 以68%的产率得到胆甾-5-烯-3-醇
  参考文献：
  名称：

  Davis, K. Joju; Bhalerao; Rao, B. Vittal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 3, p. 211 - 212

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 叔丁基锂 、 manganese(III) triacetate dihydrate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 7.5h， 生成 2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  铜催化的硼酸酯的氧化乙酰化作用：环缩醛合成的Umpolung策略。

  摘要：

  描述了硼酸酯的缩醛化的方案。该反应由铜催化，条件证明是温和的并且适合于各种官能团。我们扩展了Chan–Lam偶联，使其包含C（sp 3）亲核试剂，并将其转化为相应的缩醛。该方法允许具有反应性，酸敏感性官能团的底物正交缩醛化。

  DOI：

  10.1021/acs.joc.0c00720

文献信息

• Allyl tetrahydropyranyl ether: a versatile alcohol/thiol protecting reagent
  作者：Brijesh Kumar、Mushtaq A. Aga、Debaraj Mukherjee、Swapandeep S. Chimni、Subhash C. Taneja

  DOI：10.1016/j.tetlet.2009.09.026

  日期：2009.11

  Allyl tetrahydropyranyl ether (ATHPE) can be used as a versatile protecting reagent. In combination with NBS/I2, O-allyl group can easily be replaced by hydroxyls (including tertiary-OH) or thiols, in the molecules comprising other reactive functional groups such as halogen, nitro, acetonide and alkene under mild reaction conditions (near neutral pH and ambient temperature).

  烯丙基四氢吡喃基醚（ATHPE）可用作通用保护剂。与NBS / I 2结合使用时，在温和的反应条件下（附近），在包含其他反应性官能团（例如卤素，硝基，丙酮化物和烯烃）的分子中，O-烯丙基可以轻松地被羟基（包括叔羟基）或硫醇取代。中性pH和环境温度）。
• Chemoselective tetrahydropyranylation of alcohols and phenols using polystyrene supported aluminium chloride as a catalyst
  作者：Bahman Tamami、Kaveh Parvanak Borujeny

  DOI：10.1016/j.tetlet.2003.11.056

  日期：2004.1

  A simple, efficient and highly chemoselective method for tetrahydropyranylation of alcohols and phenols has been developed by their reaction with 3,4-dihydro-2H-pyran at room temperature in the presence of a catalytic amount of polystyrene supported AlCl3. The method is also highly selective for monoprotection of symmetrical diols.

  通过在室温下在催化量的聚苯乙烯负载的AlCl 3存在下，它们与3,4-二氢-2 H-吡喃反应，开发了一种简单，有效且高度化学选择性的醇和酚四氢吡喃基化方法。该方法对于对称二醇的单保护也是高度选择性的。
• Sulfuric Acid Adsorbed on Silica Gel. An Efficient Catalyst for the Tetrahydropyranylation of Alcohols
  作者：Flavio Chávez、Raul Godinez

  DOI：10.1080/00397919208021087

  日期：1992.1

  Abstract Sulfuric acid adsorbed on silica gel is an efficient catalyst for the tetra-hydropyranylation of alcohols and phenols. The reaction takes 1 to 10 minutes to be completed and nearly quantitative yields are obtained. The method is remarkable simple and inexpensive.

  摘要 吸附在硅胶上的硫酸是醇类和酚类四氢吡喃化反应的有效催化剂。反应需要 1 到 10 分钟才能完成并获得几乎定量的产率。该方法非常简单且便宜。
• Copper(II)chloride Catalyzed Tetrahydropyranylation of Alcohols
  作者：U. T. Bhalerao、K. Joj Davis、B. Vittal Rao

  DOI：10.1080/00397919608004611

  日期：1996.8

  A simple and efficient methodology for the tetrahydropyranylation of alcohols using catalytic amount of copper(II)chloride in dichloromethane is described The yields obtained are good to excellent.
• A versatile ruthenium catalyst for the tetrahydropyranylation of alcohols and phenols
  作者：Shengming Ma、Lulgi M. Venanzi

  DOI：10.1016/s0040-4039(00)73970-0

  日期：1993.8

  The tetrahydropyranyl derivatives of alcohols and phenols are efficiently prepared in the presence of catalytic amounts of [Ru(CH3CN)3(triphos)](OTf)2 (triphos = CH3C(CH2PPh2)3) under mild conditions, in good to excellent yields.