4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol
• 英文别名: ((4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol；[(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• 化学式: C₂₃H₃₂O₄Si
• 分子量: 400.59
• InChiKey: XMXUBCUCCBZXQX-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 tert-Butyl-((4S,5S)-5-ethynyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane
  参考文献：
  名称：

  O-Directed Free-Radical Hydrostannations of Propargyl Ethers, Acetals, and Alcohols with Ph₃SnH and Et₃B

  摘要：

  The O-directed hydrostannation of various propargyloxy substrates is reported with Ph(3)SnH/Et(3)B.

  DOI：

  10.1021/ol051936l
• 作为产物：
  描述：

  (4R,5R)-4,5-二乙氧基羰基-2,2-二甲基二氧 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol
  参考文献：
  名称：

  A convergent approach for the total synthesis of the α-glucosidase inhibitor (−)-panaxjapyne-C

  摘要：

  The stereoselective total synthesis of (-)-panaxjapyne-C was accomplished in a convergent fashion. The synthesis utilizes the readily available enantiomers L-(+)-diethyltartrate and D-(-)-diethyltartrate and involves a Cadiot-Chodkiewicz coupling reaction, and an Ohira-Bestmann reaction as the key steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.017

文献信息

• Efficient Synthesis of the C1-C9 Fragment of 7,8-O-Isopropylidene Protected Iriomoteolide 3a Derivative
  作者：Ching-Yao Chang

  DOI：10.1002/jccs.201190054

  日期：2011.2

  An efficient and stereoselective synthesis of the C1‐C9 moiety of the 7,8‐O‐isopropylidene protected iriomoteolide 3a derivative has been accomplished. In our strategy, we employed olefin cross‐metathesis of the L‐(+)‐tartaric acid derivative (((4S,5S)‐2,2‐dimethyl‐5‐vinyl‐1,3‐dioxolan‐4‐yl)methoxy)(tert‐butyl)diphenylsilane with a synthesized methyl (S)‐3‐methylhex‐5‐enate to successfully provide

  已完成7,8 - O-异亚丙基保护的iriomoteolide 3a衍生物的C1-C9部分的高效立体选择性合成。在我们的策略中，我们使用了L -（+）-酒石酸衍生物（（（4 S，5 S）-2,2-二甲基-5-乙烯基-1,3-二氧戊环-4-基）（甲氧基）（叔丁基）二苯基硅烷与合成的（S）-3-甲基己基-5-烯酸甲酯成功地提供所需片段的正确烯烃几何形状。
• [EN] ARYLOXYACETYLINDOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS<br/>[FR] ARYLOXYACÉTYLINDOLES ET ANALOGUES EN TANT QU'INHIBITEURS DE TOLÉRANCE AUX ANTIBIOTIQUES
  申请人：SPERO THERAPEUTICS INC

  公开号：WO2016112088A1

  公开（公告）日：2016-07-14

  The disclosure provides compounds and pharmaceutical compositions of aryloxyacetylindoles compounds and analogs useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

  该披露提供了芳基氧乙酰基吲哚化合物及类似物的化合物和药物组合物，用于治疗慢性和急性细菌感染。其中某些化合物是一般式(I)（I）的化合物或其药用可接受的盐或前药。该披露的某些化合物是MvfR抑制剂。MvfR抑制剂减少抗生素耐药细菌菌株的形成，对治疗革兰氏阴性细菌感染和减少铜绿假单胞菌的毒力有用。该披露还提供了治疗受试者细菌感染的方法，包括铜绿假单胞菌感染。
• Total Synthesis of Everninomicin 13,384-1—Part 2: Synthesis of the FGHA2 Fragment
  作者：K. C. Nicolaou、Helen J. Mitchell、Konstantina C. Fylaktakidou、Rosa Maria Rodríguez、Hideo Suzuki

  DOI：10.1002/1521-3765(20000901)6:17<3116::aid-chem3116>3.0.co;2-8

  日期：2000.9.1

  The stereoselective synthesis of everninomicin's 13,384-1 (1) FGHA2 fragment (2) in a suitable form for incorporation into the final target (1) is described. The construction of the FG 1,1'-disaccharide linkage relied on a new method based on tin-acetal chemistry, while for the GH orthoester bridge, a number of approaches were explored. Final success for the latter construction came when a novel 1

  描述了以合适的形式结合到最终靶标（1）中的everninomicin's 13,384-1（1）FGHA2片段（2）的立体选择性合成。FG 1,1'-二糖键的构建依赖于基于锡-缩醛化学的新方法，而对于GH原酸酯桥，则探索了许多方法。后一种结构的最终成功是通过将新的1,2-苯基硒代迁移反应应用于环G和H偶联，随后是乙烯酮缩醛和原酸酯的形成。
• Further Development of the Tin-Catalyzed Transcarbamoylation Reaction
  作者：Yoshiyasu Ichikawa、Tomoyuki Hasegawa、Takahiro Minami、Hiroshi Sato、Yukinori Morishita、Rika Ochi、Toshiya Masuda

  DOI：10.1055/s-0040-1708020

  日期：2020.8

  Studies carried out to further develop tin-catalyzed trans­carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-­catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate

  为进一步开发锡催化的氨基甲酸酯化反应而进行的研究表明，在烯丙基氰酸酯到异氰酸酯重排的背景下，肉桂醇的氨基甲酸酯化可以有效地在10克规模上进行，并且锡催化的氨基甲酸酯化是一种有价值的替代方法该方法使用三氯乙酰基异氰酸酯。此外，在锡催化的转氨甲酰化反应中发现氨基甲酸甲酯是一种经济的氨基甲酰基供体，该氨基甲酸酯显示出广泛的官能团耐受性，并简化了后处理程序。最后，开发了一种独特的合成方法来制备氨基甲酸酯系萜烯糖结合物。
• An Efficient Synthesis of Carbamates by Tin-Catalyzed Transcarbamoylation Reactions of Primary and Secondary Alcohols
  作者：Yoshiyasu Ichikawa、Yukinori Morishita、Shuhei Kusaba、Naoto Sakiyama、Yasunori Matsuda、Keiji Nakano、Hiyoshizo Kotsuki

  DOI：10.1055/s-0030-1258102

  日期：2010.7

  A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 °C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance.

  已经开发了一种基于锡催化氨基甲酰化过程合成氨基甲酸酯的新方法。伯醇和仲醇与氨基甲酸苯酯在 90 °C 的甲苯中在锡催化剂存在下顺利进行反应，以良好的产率生成相应的氨基甲酸酯。这种温和的方法表现出广泛的官能团耐受性。