(R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol
• 英文别名: (R)-1-O-tert-butyldiphenylsilyl-1,3-butanediol；(R)-4-(tert-butyldiphenylsilyloxy)butan-2-ol；(R)-1-t-butyldiphenylsiloxy-3-butanol；(2R)-4-[tert-butyl(diphenyl)silyl]oxybutan-2-ol
• 化学式: C₂₀H₂₈O₂Si
• 分子量: 328.527
• InChiKey: NZRAEAHCRDZSLJ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  [EN] PRODRUGS WITH 1-(DISULFANYL)ALKYLOXY-CARBONYL UNITS
  [FR] PROMÉDICAMENTS À MOTIFS 1-(DISULFANYL)ALKYLOXY-CARBONYLE

  摘要：

  The invention is in the field of medical sciences. It provides new pharmaceutical methods and preparations. The invention relates to methods for improving the pharmacokinetic, physicochemical or pharmaceutical properties of drugs by converting the drug into a promoiety-containing 1-substituted disulfanylalkyl carbonate, thiocarbamate or carbamate prodrug. In particular, the invention relates to methods for improving the solubility, permeability, stability and/or oral bioavailability of a drug by converting the drug into a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate prodrug. The invention also provides new compositions comprising a drug covalently attached to a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate. More in particular, the invention relates to a method for increasing the oral bioavailability of a drug by covalently attaching a promoiety-containing 1-disulfanylalkyloxycarbonyl unit to a hydroxyl or amine containing drug in which the promoiety contains a 1-0-, 1-S-, 6-0- or 6-S-linked monosaccharide. Formula I

  公开号：

  WO2022271018A1
• 作为产物：
  描述：

  (R)-tert-butyldiphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butoxy)silane 在 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol
  参考文献：
  名称：

  利用锂化/硼烷基化反应短立体选择性合成疫霉通用交配激素α1

  摘要：

  毒性植物病原菌疫霉的通用交配激素α1已通过12个步骤合成，总产率为28％。密钥C  C键形成步骤涉及使用两个锂化/硼基化反应来耦合在一起对映体富集积木，其中之一也设置在C11叔醇的立体化学。详细分析表明，目标分子的非对映异构体纯度> 91％，是迄今为止获得的最高纯度。

  DOI：

  10.1002/anie.201400714

文献信息

• Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor
  作者：Masamichi Tanaka、Junki Nashida、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.orglett.6b00926

  日期：2016.5.6

  in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

  在糖基受体衍生的硼酸酯存在下，使用1,2-脱水甘露糖供体和单醇受体进行β-立体选择性甘露糖基化。反应在温和条件下平稳进行，以中等至高产率提供具有高立体选择性的相应β-甘露糖苷。此外，本糖基化方法已成功地应用于阿莫莫尼脂A的全合成。
• Iridium-Catalyzed Asymmetric Hydrogenation of Vinyl Ethers
  作者：Ye Zhu、Kevin Burgess

  DOI：10.1002/adsc.200700546

  日期：2008.5.5

  A carbene-oxazoline catalyst 1 proved to be an effective catalyst for reduction of an enol ether that the literature suggested could not be hydrogenated effectively by P,N-Ir catalysts. Thus, a series of ester and alcohol substrates were hydrogenated using catalyst 1. Good to excellent enantioselectivities and high conversions were obtained.

  卡宾-恶唑啉催化剂1被证明是还原烯醇醚的有效催化剂，文献认为该催化剂不能被P，N- Ir催化剂有效地氢化。因此，使用催化剂1将一系列酯和醇底物氢化。获得良好至优异的对映选择性和高转化率。
• Enantioselective Intramolecular Aldehyde α-Alkylation with Simple Olefins: Direct Access to Homo-Ene Products
  作者：Robert J. Comito、Fernanda G. Finelli、David W. C. MacMillan

  DOI：10.1021/ja4047312

  日期：2013.6.26

  A highly selective method for the synthesis of asymmetrically substituted carbocycles and heterocycles from unactivated aldehyde-olefin precursors has been achieved via enantioselective SOMO-catalysis. Addition of a catalytically generated enamine radical cation across a pendent olefin serves to establish a general asymmetric strategy toward the production of a wide range of formyl-substituted rings

  通过对映选择性 SOMO 催化，实现了一种从未活化的醛-烯烃前体合成不对称取代的碳环和杂环的高选择性方法。在悬垂烯烃上添加催化生成的烯胺自由基阳离子有助于建立一般的不对称策略，以产生广泛的具有烯烃转位的甲酰基取代的环。从概念上讲，这种新颖的机制允许直接访问“均烯”型产品。
• A Short Enantiosynthesis ofDioxaspiroacetalic Semiochemicals by Using Chiral Building-Blocksfrom<i>rac</i>-1,n-Alkanediols by Lipase-Mediated Resolution
  作者：Isidoro Izquierdo、María T. Plaza、Miguel Rodríguez、Juan A. Tamayo

  DOI：10.1055/s-2003-40205

  日期：——

  (2R,6S,8R)-2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane (la) and its enantiomer 1b, have been synthesized by Wittig's methodology using the ylide from acetone-1,3-bis(triphenylphosphonium) chloride and the appropriately protected aldehydes from chiral 1,3-butanediols. The latter are prepared by a chemoenzymatic resolution procedure.

  (2R,6S,8R)-2,8-Dimethyl-1,7-dioxaspiro[5.5] undecane (la) 及其对映异构体 1b 已通过 Wittig 的方法使用来自 acetone-1,3-bis(triphenylphosphonium) 的叶立德合成) 氯化物和适当保护的醛免受手性 1,3-丁二醇的影响。后者是通过化学酶拆分程序制备的。
• 2,3,5-trisubstituted pyridines as inhibitors of cyclooxygenase-2
  申请人：Merck Frosst Canada & Co.

  公开号：US06046217A1

  公开（公告）日：2000-04-04

  The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  本发明涵盖了式I的新化合物，以及治疗环氧合酶-2介导的疾病的方法，包括向需要此类治疗的患者施用式I化合物的非毒性治疗有效量。##STR1## 本发明还涵盖了治疗环氧合酶-2介导的疾病的某些药物组合物，其中包括式I的化合物。