(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-2,3-dihydropyran-6-one | 143144-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-2,3-dihydropyran-6-one
• CAS: 143144-73-4
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: FSFVCAVRPMPEOE-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-2,3-dihydropyran-6-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以85%的产率得到rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  酚类递质反应及其在天然产物合成中的应用

  摘要：

  芳ø -Δ 2 -glycosides通过Ferrier的反应合成。用Ag（DPAH）2氧化除去对甲氧基苯基。

  DOI：

  10.1016/0040-4039(94)88297-5
• 作为产物：
  描述：

  4'-methoxyphenyl 4-O-acetyl-2,3,6-trideoxy-1-O-α-L-erythro-hex-2-enopyranoside 在 咪唑 、 甲醇 、 manganese(IV) oxide 、 pyridine-2,6-dicarboxylic acid, Ag(II) chelate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  酚类递质反应及其在天然产物合成中的应用

  摘要：

  芳ø -Δ 2 -glycosides通过Ferrier的反应合成。用Ag（DPAH）2氧化除去对甲氧基苯基。

  DOI：

  10.1016/0040-4039(94)88297-5

文献信息

• Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
  作者：Tharun K. Kotammagari、Rajesh G. Gonnade、Asish K. Bhattacharya

  DOI：10.1021/acs.orglett.7b01525

  日期：2017.7.7

  A one-pot biomimetic synthesis of (−)-angiopterlactone B and its enantiomer (+)-angiopterlactone B has been accomplished via TBAF-catalyzed tandem ring contraction followed by oxa-Michael/Michael addition sequence. Comparison of specific optical rotations, absolute configurations, and CD spectra of natural, synthesized (−)-angiopterlactone B and (+)-angiopterlactone B unequivocally proves that the

  已经通过TBAF催化的串联环收缩和oxa-Michael / Michael加成序列完成了一锅仿生合成（-）-angiopterlactone B和其对映异构体（+）-angiopterlactone B的过程。比较天然，合成的（-）-血管内酯B和（+）-血管内酯B的比旋光度，绝对构型和CD光谱，可以明确地证明分离出的血管内酯B必须是左旋的。迄今未发现的天然产物18和20以及血管内酯B的类似物的合成证明了该方法的多功能性。
• A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring-closing metathesis
  作者：Lizhi Zhu、James P. Kedenburg、Ming Xian、Peng George Wang

  DOI：10.1016/j.tetlet.2004.12.014

  日期：2005.1

  A systematic synthetic strategy has been developed for producing uncommon sugars. This method involved kinetic resolution allylic alcohol followed by ring-closing-metathesis (RCM) to generate optical pure lactones as the common precursors. After further derivatization, four representative uncommon sugar units were successfully synthesized. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis, structure and chiroptical properties of isoxazolidin-5-ones
  作者：Jadwiga Frelek、Irma Panfil、Przemyslaw Gluzinski、Marek Chmielewski

  DOI：10.1016/s0957-4166(96)00449-1

  日期：1996.12

  Several isoxazolidin-5-ones were synthesized in an addition - rearrangement reaction from corresponding sugar lactones and hydroxylamines. The sign of the Cotton effect at ca. 220 nm can be correlated to the absolute configuration of the stereogenic center at C3 and can be predicted by Weigang's sector rule. X-ray diffraction study performed for 11 and 12 confirms the configuration at C3 to be 3S and 3R, respectively. Copyright (C) 1996 Elsevier Science Ltd
• A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal
  作者：Guisheng Zhang、Lei Shi、Qingfeng Liu、Xiaobing Liu、Lu Li、Jingmei Wang

  DOI：10.1016/j.tetlet.2007.03.062

  日期：2007.5

  An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-L-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3-OEt2-induced peroxidation of rhamnal to construct key intermediate alpha,beta-unsaturated lactone as the common precursor. After further derivatization, four 3-azido hexoses were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.
• Reductive aromatization of quinols. New convenient methods for the regiospecific synthesis of p-hydroxy C-aryl glycals
  作者：Kathlyn A. Parker、Craig A. Coburn、Paul D. Johnson、Paul Aristoff

  DOI：10.1021/jo00046a049

  日期：1992.9