(6R)-6-methyltetrahydropyran-2-ol | 194795-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (6R)-6-methyltetrahydropyran-2-ol
• 英文别名: (R)-6-methyl δ-lactol；(6R)-6-methyloxan-2-ol
• CAS: 194795-88-5
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: XCNWVNNDBZRDEA-LWOQYNTDSA-N

物化性质

• 沸点：
  180.2±8.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R)-6-methyltetrahydropyran-2-ol 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.5h， 生成 ((S)-1-Dimethylcarbamoyl-ethyl)-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  6-Methyl δ-lactol derived chiral glycine equivalents for the asymmetric synthesis of protected α-amino amides

  摘要：

  Two new delta-lactol derived chiral glycine equivalents have been prepared in one-pot processes in good yields from the known 6-methyltetrahydropyran-2-ol. Alkylation proceeds in moderate to good yields and moderate to good selectivities under experimentally simple conditions. The lactol chiral auxiliary is readily removed under mild acidic conditions to give N-Cbz protected alpha-amino amides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.026
• 作为产物：
  描述：

  5-氧代己酸 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (6R)-6-methyltetrahydropyran-2-ol
  参考文献：
  名称：

  Biocatalyst-Mediated Efficient Preparation of Highly Enantiomerically Enriched (R)-5-Hexanolide

  摘要：

  本文描述了生物催化剂介导的高效制备高对映体富集度的(R)-5-己内酯（1）的方法。通过Yamadazyma farinosa IFO 10896对5-氧代己酸的对映选择性还原，随后经脂酶催化的动力学拆分，得到了产率为62%、对映体过量值高达99.7%的(R)-1。

  DOI：

  10.1055/s-1997-972

文献信息

• Origin of Diastereocontrol in the Oxy-Michael Reactions of δ-Lactol Anions: A Computational and Experimental Study
  作者：Robert D. Richardson、Felix A. Hernandez-Juan、John W. Ward、Darren J. Dixon

  DOI：10.1002/chem.200801368

  日期：2008.10.29

  energy refinements. The resulting proposed model for the origins of stereocontrol in this reaction has been tested by experiment. The reactions lead to a high cis diastereoselectivity across the THP ring due to the preference for both the alkoxide and the 6-substituent to sit equatorial in the alkylation transition structure. In the oxy-Michael addition of these lactolates to beta-substituted nitroolefins

  通过从头算（MP2）能量优化的密度泛函（B3LYP）计算，研究了“裸” 6-取代的δ-乳酸酯的烷基化和迈克尔加成中的非对映选择性。已经通过实验测试了所提出的用于该反应中立体控制起源的模型。由于偏爱醇盐和6-取代基都位于烷基化过渡结构中的赤道，该反应导致整个THP环具有很高的顺式非对映选择性。在将这些乳酸酯的氧基-迈克尔加成到β-取代的硝基烯烃中时，我们提出对硝基的高非对映选择性β-是空间，立体电子和溶剂化因子结合的结果。
• CONJUGATES OF IMMUNE CELL SPECIFIC MACROLIDE COMPOUNDS WITH ANTI-INFLAMMATORY COMPOUNDS FOR IMPROVED CELLULAR TARGETING OF ANTI-INFLAMMATORY THERAPY
  申请人：GlaxoSmithKline istrazivacki centar Zagreb d.o.o.

  公开号：EP1351973B1

  公开（公告）日：2010-03-31
• ENZYMATIC SYNTHESIS OF ACTIVE PHARMACEUTICAL INGREDIENT AND INTERMEDIATES THEREOF
  申请人：LEK Pharmaceuticals d.d.

  公开号：EP2655650B1

  公开（公告）日：2017-12-20
• BIOCONJUGATES OF HETEROCYCLIC COMPOUNDS
  申请人：Hao Xiujuan

  公开号：US20190339283A1

  公开（公告）日：2019-11-07

  The invention provides bioconjugates of heterocylic compounds such as S-adenosylmethionine and S-adenosylhomocysteine with biotin or digoxigenin. The bioconjugates also include carbon and nitrogen linker moieties of varying length that are used to attach such compounds to biotin or digoxigenin. The conjugates are useful in immunoassays. The invention provides a method for detecting SAM and SAH, comprising the steps of: (a) preparing the following components: (i) bio-conjugates of SAM, SAM analogs or SAH; (ii) an europium, a terbium cryptate or other fluorophore as a donor that has a specific ligand for the tracer in the bio-conjugates of (i); (iii) an acceptor fluorescent dye that has the excitation spectra overlap those of donor's emissions and has an antibody specific for SAM or SAH labeled; (b) addition of the biological fluid containing said SAM or SAH; and (c) spectroscopic measurement of the fluorescence of the donor and the fluorescence of from the acceptor.
• [EN] MACROLIDE COMPOUNDS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPOSÉS MACROLIDES ET PROCÉDÉS POUR LEUR FABRICATION ET LEUR UTILISATION
  申请人：RIB X PHARMACEUTICALS INC

  公开号：WO2008143729A2

  公开（公告）日：2008-11-27

  [EN] The present invention provides a family of branched amide containing macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, antiproliferative, anti-inflammatory, and prokinetic agents.
  [FR] La présente invention concerne une famille d'amide ramifiée contenant des composés macrocycliques utiles comme agents thérapeutiques. En particulier, ces composés sont utiles comme agents anti-infectieux, anti-prolifération, anti-inflammatoire et procinétiques.