(S)-1-三苯基甲氧基丙烷-2-醇 | 85550-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: (S)-1-三苯基甲氧基丙烷-2-醇
• 英文名称: (S)-1-(trityloxy)propan-2-ol
• 英文别名: 2-Propanol, 1-(triphenylmethoxy)-, (2S)-；(2S)-1-trityloxypropan-2-ol
• CAS: 85550-19-2
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: JODCGDLBQGFBTI-SFHVURJKSA-N

物化性质

• 沸点：
  447.0±40.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (S)-1-三苯基甲氧基丙烷-2-醇 在 吡啶 、 sodium hydride 作用下， 反应 76.0h， 生成 (R,R)-bis(1-methyl-2-triphenylmethyloxy)ethyl ether
  参考文献：
  名称：

  Licandro, Emanuela; Maiorana, Stefano; Manzotti, Raffaella, Gazzetta Chimica Italiana, 1997, vol. 127, # 12, p. 815 - 818

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯甲基-(S)-缩水甘油醚 在 copper(l) iodide 、 乙烯基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(S)-1-三苯基甲氧基丙烷-2-醇
  参考文献：
  名称：

  Macrocyclic Bisindolylmaleimides:  Synthesis by Inter- and Intramolecular Alkylation

  摘要：

  Macrocyclic bisindolylmaleimides 1-4 have been identified as competitive reversible inhibitors of PKC beta(1) and beta(2) and are being advanced to the clinic for evaluation as a treatment of retinopathy associated with diabetic complications. Highly convergent and stereoselective syntheses of 1-4 have been developed. The key synthetic step involves intermolecular alkylation of symmetrical bisindolylmaleimide 9 with chiral bisalkylating agent 8c and is amenable to the preparation of multikilogram quantities of these compounds. The synthetic sequence to 1, the most active compound, proceeds in 11 steps and 26% overall yield (>98% ee) from (R)-1-chloro-2,3-propanediol. No chromatographic purifications are required throughout the process and the final product is isolated in >97% purity after crystallization from DMF/MeOH. Synthesis of 1-4 by intramolecular alkylation proved less efficient, requiring 1? steps and affording 1-4 in lower overall yields of 6.0-8.5%.

  DOI：

  10.1021/jo971980h

文献信息

• Synthesis and Antiretroviral Evaluation of New Alkoxy and Aryloxy Phosphate Derivatives of 3‘-Azido-3‘-deoxythymidine
  作者：Andrew Tsotinis、Theodora Calogeropoulou、Maria Koufaki、Charikleia Souli、Jan Balzarini、Erik De Clercq、Alexandros Makriyannis

  DOI：10.1021/jm950777g

  日期：1996.1.1

  results of the biological tests indicate that analogs with a methyl group alpha to the phosphate moiety (11c,d) exhibit a marked degree of stereoselectivity with regard to their anti-HIV activity. Also, replacement of the long alkyl chain with aromatic groups in the oxyalkyl ether phospholipid-AZT conjugates leads to substantially more potent compounds (11e-g) with an anti-HIV activity comparable to that

  合成了一系列新的醚脂质3'-叠氮基3'-脱氧胸苷（AZT）缀合物（11a-g），并评估了其抗HIV活性。通过合成在分子的脂质部分（11a-d）中带有烷氧基丙醇的AZT缀合物，检查了手性对抗病毒活性的影响。另外，烷氧基乙基脂质脂质-AZT类似物的长烷基链被芳族基团（11e-g）代替，并且报道了这种结构修饰对活性的影响。生物学测试的结果表明，相对于其抗HIV活性，在磷酸部分（11c，d）处具有甲基的甲基类似物表现出显着的立体选择性。还，
• Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
  作者：Jun Ho Choi、Yoon Kyung Choi、Yu Hwan Kim、Eun Sil Park、Eun Jung Kim、Mahn-Joo Kim、Jaiwook Park

  DOI：10.1021/jo0355799

  日期：2004.3.1

  tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In

  Aminocyclopentadienyl钌复合物，其可以用作常温消旋催化剂与在动态动力学拆分仲醇的（DKR），脂肪酶是从环戊-2,4- dienimines合成的Ru 3（CO）12，和CHCl 3： [2,3,4,5-PH 4（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上4：R =我-Pr; 5：R = ñ -Pr; 6：R =吨-Bu ），[2,5-ME 2 -3,4--PH 2（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上7：R = i -Pr; 8：R = PH），和[2,3,4,5-PH 4（η 5 -C 4 CNHAr）]的Ru（CO）2 Cl（上9：Ar为p -NO 2 ç 6 ħ 4 ; 10： Ar ＝p- ClC 6 H 4；11：Ar ＝ Ph；12：Ar ＝p- OMeC 6 H 4；13：Ar ＝p- NMe 2 C 6 H 4）。外消旋
• Molecular Structure of Helical Supramolecular Dendrimers
  作者：Mihai Peterca、Virgil Percec、Mohammad R. Imam、Pawaret Leowanawat、Kentaro Morimitsu、Paul A. Heiney

  DOI：10.1021/ja806524m

  日期：2008.11.5

  The molecular structure of helical supramolecular dendrimers generated from self-assembling dendrons and dendrimers and from self-organizable dendronized polymers was elucidated for the first time by the simulation of the X-ray diffraction patterns of their oriented fibers. These simulations were based on helical diffraction theory applied to simplified atomic helical models, followed by Cerius2 calculations

  通过模拟定向纤维的 X 射线衍射图，首次阐明了由自组装树枝状聚合物和树枝状聚合物以及自组织树枝状聚合物产生的螺旋超分子树枝状聚合物的分子结构。这些模拟基于应用于简化原子螺旋模型的螺旋衍射理论，然后是基于其完整分子螺旋结构的 Cerius2 计算。筛选了数百个样品，直到包含 14 个超分子树枝状聚合物和树枝状聚合物的库在其定向纤维的 X 射线衍射图中提供了足够数量的螺旋特征。这种技术组合提供了单 9(2) 和 -11(3) 螺旋、三重 6(1)、-8(1)、-9(1) 和 -12(1) 螺旋的示例，以及由冠状树枝状大分子、空心和非空心超分子冠状树枝状大分子、空心和非空心超分子盘状树枝状大分子以及空心和非空心超分子和大分子螺旋状结构组装而成的八角 32(1) 螺旋。这里阐述的用于确定分子螺旋结构的方法是从结构生物学领域移植过来的，将适用于其他类别的合成螺旋组件。螺旋超分子组件的分子结构的确定有
• Helical and Flat Structures from Chiral Dendronized Rectangular Oligo(phenylene ethynylene)s
  作者：Fátima García、Fátima Aparicio、Marco Marenchino、Ramón Campos-Olivas、Luis Sánchez

  DOI：10.1021/ol101673z

  日期：2010.10.1

  The synthesis of two chiral amphiphiles and their self-assembling features in solution and onto surfaces is reported. The different degree of interdigitation of the paraffinic substituents has an enormous influence in the chirality of the aggregates. Thus, while oligo(phenylene ethynylene) 1 shows a bisignated Cotton effect in solution and P-type helices onto surfaces, compound 2 lacks in any dichroic

  报道了两种手性两亲物的合成及其在溶液中和表面上的自组装特征。链烷烃取代基的相互交叉程度不同，对聚集体的手性有很大影响。因此，尽管低聚（亚苯基亚乙炔基）1在溶液中显示出双向作用的棉花效应，并且在表面上呈现P型螺旋，但化合物2在室温下没有任何二向色性反应，并且自组装成扁平带。
• Continuous-Flow Synthesis of (<i>R</i> )-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir
  作者：Nicolas S. Suveges、Anderson A. Rodriguez、Carla C. Diederichs、Stefania P. de Souza、Raquel A. C. Leão、Leandro S. M. Miranda、Bruno A. C. Horta、Sérgio F. Pedraza、Otavio V. de Carvalho、Karla C. Pais、José H. C. Terra、Rodrigo O. M. A. de Souza

  DOI：10.1002/ejoc.201800345

  日期：2018.6.22

  (R)‐Propylene carbonate is an important intermediate in the synthesis of tenofovir alafenamide fumarate (TAF) and tenofovir disoproxil fumarate (TDF) from glycerol. TAF and TDF present a chiral secondary hydroxy derivative, which can be obtained by a seven‐step chemo‐enzymatic continuous‐flow strategy that yields (R)‐propylene carbonate in good‐to‐excellent yields and excellent selectivity.

  （R）-碳酸亚丙酯是从甘油合成替诺福韦alafenamide富马酸酯（TAF）和替诺福韦二吡呋酯富马酸酯（TDF）的重要中间体。TAF和TDF呈现一种手性仲羟基衍生物，可以通过七步化学酶促连续流动策略获得，该策略可以以优异的产率和优异的选择性产生碳酸（R）-碳酸亚丙酯。