(+)-1-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythritol | 164105-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-1-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythritol
• CAS: 164105-98-0
• 化学式: C₂₃H₃₂O₄Si
• 分子量: 400.59
• InChiKey: XMXUBCUCCBZXQX-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 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：
  0.48
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-1-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythritol 在 四氧化锇 、 四丙基高钌酸铵 、 4 A molecular sieve 、 水 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 159.0h， 生成 6-O-(t-butyldiphenylsilyl)-L-allono-1,4-lactone
  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：

  ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 在 咪唑 、 甲醇 、 SAM II_. lipase 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 54.33h， 生成 (+)-1-O-(t-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythritol
  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

• Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity
  作者：Junki Nashida、Nobuya Nishi、Yoshiaki Takahashi、Chigusa Hayashi、Masayuki Igarashi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.joc.8b00032

  日期：2018.7.6

  The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated

  由烷基硼酸催化的β-甘露糖基化反应立体选择性地构建的策略性设计的关键关键中间体可以有效，系统地完成具有不同烷基链长度的甘露糖基赤藓糖醇脂质（MEL）的20个均质成员的全合成。另外，评估了它们对革兰氏阳性细菌的抗菌活性。我们的结果表明，不仅烷基链的长度，而且甘露糖部分上的Ac基团的模式也是抗菌活性的重要因素。
• Synthesis of Mannosylerythritol Lipid Analogues and their Self‐Assembling Properties, Recovery Effects on Damaged Skin Cells, and Antibacterial Activity
  作者：Takanori Kondo、Chihiro Yasui、Ikkei Miyajima、Taisuke Banno、Kouichi Asakura、Tokuma Fukuoka、Kazunori Ushimaru、Maito Koga、Azusa Saika、Tomotake Morita、Yoshiaki Takahashi、Chigusa Hayashi、Masayuki Igarashi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/chem.202201733

  日期：2022.10.4

  Antibacterial artificial sugar-based material: Synthesis of three types of mannosylerythritol lipid (MEL)-D analogues with decanoyl groups, β-GlcEL-D, β-GlcEL-D, and α-MEL-D, was accomplished. Their self-assembling properties, recovery effects on damaged skin cells, and antibacterial activity were evaluated. The results indicated α-MEL-D is a promising artificial sugar-based material candidate for

  抗菌人工糖基材料：完成了三种具有癸酰基的甘露糖基赤藓糖醇脂质 (MEL)-D 类似物 β-GlcEL-D、β-GlcEL-D 和 α-MEL-D 的合成。评估了它们的自组装特性、对受损皮肤细胞的恢复效果和抗菌活性。结果表明，α-MEL-D是一种很有前途的人造糖基材料，具有抗菌活性，可增强角质层的屏障功能。
• 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).