(-)-4-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-L-erythrose | 164105-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-4-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-L-erythrose
• 英文别名: (4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde；(4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 164105-99-1
• 化学式: C₂₃H₃₀O₄Si
• 分子量: 398.574
• InChiKey: IARLEQVUVIJKBD-RTWAWAEBSA-N

物化性质

• 沸点：
  449.0±43.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-4-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-L-erythrose 在 四氧化锇 、 水 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 10.5h， 生成 (+)-methyl 6-O-(t-butyldiphenylsilyl)-4,5-O-isopropylidene-L-galactonate
  参考文献：
  名称：

  Pottie, M.; Lathauwer, G. De; Vandewalle, M., Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 5-6, p. 285 - 294

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-1-O-acetyl-2,3-O-isopropylidene-L-erythritol 在 咪唑 、 甲醇 、 四丙基高钌酸铵 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.33h， 生成 (-)-4-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-L-erythrose
  参考文献：
  名称：

  Pottie, M.; Lathauwer, G. De; Vandewalle, M., Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 5-6, p. 285 - 294

  摘要：

  DOI：

文献信息

• Remote Stereocontrol in the Ireland–Claisen Rearrangement by δ-Alkoxy Group
  作者：Hye Joon Lee、Joshua J. Gladfelder、Armen Zakarian

  DOI：10.1021/acs.joc.3c00535

  日期：2023.6.2

  Remote stereocontrol in the Ireland–Claisen rearrangement using a chiral acetonide that serves as internal stereocontrol element is an effective and general method for chirality transfer from a δ-hydroxyl group in the allylic alcohol unit. This strategy circumvents the need for redundant chirality at the α-position allylic alcohol, while simultaneously producing a terminal alkene that can streamline

  使用手性丙酮化合物作为内部立体控制元素的 Ireland-Claisen 重排中的远程立体控制是从烯丙醇单元中的 δ-羟基进行手性转移的有效且通用的方法。该策略避免了对 α 位烯丙醇的冗余手性的需要，同时产生可以简化合成应用和复杂分子合成计划的末端烯烃。
• Total Synthesis, Revised Structure, and Biological Evaluation of Elgonene B and Analogues
  作者：Sudip Mandal、Dora Mahananda、Sourav Dey、Ruthrotha Selvi Bharathavikru、Barla Thirupathi

  DOI：10.1021/acs.jnatprod.3c00988

  日期：2024.1.26

  Herein, we report the first total synthesis of elgonene B and its congeners, thus resulting in a revision of the configuration at the C-6 carbon of the originally proposed structure of elgonene B. This synthetic approach demonstrates the utility of several important reactions such as the chiral oxazaborolidinium ion-catalyzed Diels–Alder reaction, Ando’s Horner–Wadsworth–Emmons olefination, and the

  在此，我们报告了 elgonene B 及其同系物的首次全合成，从而对最初提出的 elgonene B 结构的 C-6 碳构型进行了修改。这种合成方法证明了几个重要反应的实用性，例如手性恶唑硼烷鎓离子催化的 Diels-Alder 反应、Ando 的 Horner-Wadsworth-Emmons 烯化反应和分子间 Nozaki-Hiyama-Kishi 反应是关键步骤。此外，该研究还探讨了 elgonene B 及其同源物的细胞毒性和抗菌活性 ( 1 – 4 )。
• Investigation of Diastereoselective Acyclic α-Alkoxydithioacetal Substitutions Involving Thiacarbenium Intermediates
  作者：Michel Prévost、Starr Dostie、Marie-Ève Waltz、Yvan Guindon

  DOI：10.1021/jo502181a

  日期：2014.11.7

  Reported herein is an experimental and theoretical study that elucidates why silylated nucleobase additions to acyclic alpha-alkoxythiacarbenium intermediates proceed with high 1,2-syn stereocontrol (anti-Felkin-Anh), which is opposite to what would be expected with corresponding activated aldehydes. The acyclic thioaminals formed undergo intramolecular cyclizations to provide nucleoside analogues with anticancer and antiviral properties. The factors influencing the selectivity of the substitution reaction have been examined thoroughly. Halothioether species initially form, ionize in the presence (low dielectric media) or absence (higher dielectric media) of the nucleophile, and react through S(N)2-like transition structures (TS A and D), where the a-alkoxy group is gauche to the thioether moiety. An important, and perhaps counterintuitive, observation in this work was that calculations done in the gas phase or low dielectric media (toluene) are essential to locate the product- and rate-determining transition structures (C-N bond formation) that allow the most reasonable prediction of selectivity and isotope effects for more polar solvents (THF, MeCN). The triangle triangle G +/- (G(TSA)-(TSD)) obtained in silico are consistent with the preferential formation of 1,2-syn product and with the trends of stereocontrol displayed by 2,3-anti and 2,3-syn alpha,beta-bis-alkoxydithioacetals.
• Synthesis of dl-cis- and (4R,5R)-trans-7-[2,2-dimethyl-4-(phenylsulfonyl)-aminomethyl-1,3-dioxolan-5-yl]-5(Z)-heptenoic acid analogues as platelet thromboxane A2 receptor antagonist
  作者：D Komiotis、S PananookoolnJ、K Zaw、JP Dieter、GC Le Breton、DL Venton

  DOI：10.1016/0223-5234(96)88240-7

  日期：1995.1

  The title compounds have been synthesized and their in vitro thromboxane A(2) (TxA(2)) receptor antagonist activity evaluated. Both cis and trans isomers (1, 2) were shown to specifically inhibit submaximal human platelet aggregation induced by 225 nM U46619 in a dose-dependent manner with an IC50 of 1 mu M. The concentration of 1 and 2 required to completely block maximal aggregation induced by 3 mu M U46619 was 3 mu(M).
• Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol
  作者：Subhendu Das、Tapan Kumar Kuilya、Rajib Kumar Goswami

  DOI：10.1021/acs.joc.5b00972

  日期：2015.6.19

  A concise and convergent route for stereoselective total synthesis of promising anticancer natural lipid mycalol has been achieved using cheap and readily available L-arabinose as a chiral pool. The notable features of our synthesis comprised regioselective Wacker oxidation, Sharpless asymmetric dihydroxylation, Julia-Kocienski olefination, Wittig olefination, Zipper reaction, and Sonogashira reaction. Comparison of the spectroscopic data on a series of isomers supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.