(2R,3R)-3-(4-methoxybenzyloxy)-2-methyl-1-butanal | 236401-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-(4-methoxybenzyloxy)-2-methyl-1-butanal
• 英文别名: (2R,3R)-3-((4-methoxybenzyl)oxy)-2-methylbutanal；(2R,3R)-3-[(4-methoxyphenyl)methoxy]-2-methylbutanal
• CAS: 236401-59-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: SQGISWQDHFUXQO-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (2R,3R)-3-(4-methoxybenzyloxy)-2-methyl-1-butanal 在 W-2 Raney nickel 草酰氯 、 氯代二环己基硼烷 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 81.0h， 生成 (2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c
• 作为产物：
  描述：

  (2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate 在 sodium tetrahydroborate 、 sodium periodate 、 三氟甲磺酸 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 9.5h， 生成 (2R,3R)-3-(4-methoxybenzyloxy)-2-methyl-1-butanal
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c

文献信息

• Polyoxygenated Tertiary Alcohols: A Kiyooka Approach
  作者：Daniel Lücke、Markus Kalesse

  DOI：10.1002/chem.201902589

  日期：2019.8

  the stereoselective synthesis of tertiary alcohols is presented. This approach allows for the incorporation of different substituents at all three remaining positions at the chiral center bearing the tertiary alcohol. To demonstrate the validity of this approach different chiral alcohols were depicted and the relationship of double bond geometry of the ketene acetal and the diastereoselectivity was

  介绍了用于立体选择性合成叔醇的Kiyooka aldol方法。该方法允许在带有叔醇的手性中心的所有三个剩余位置处引入不同的取代基。为了证明该方法的有效性，描述了不同的手性醇，并建立了乙烯酮缩醛的双键几何结构与非对映选择性的关系。
• Synthesis of the C(7)-C(20) Fragment of Spirotoamides A, B and C
  作者：Allan Rossini、Luiz Dias

  DOI：10.21577/0103-5053.20190126

  日期：——

  This work describes the preparation of the C(7)-C(20) fragment of spirotoamides A to C in a very elegant fashion, achievement very high levels of stereocontrol. The synthesis has been accomplished by a sequence involving 14 steps (0.36% overall yield, average of 81% for each step) in high diastereo and enantioselectivity, employing, as determining steps, asymmetric Mukaiyama and boron-mediated 1,5-anti promoted aldol reactions between alpha-methyl-beta-hydroxyketones and aldehydes.
• Chondramide C: Synthesis, Configurational Assignment, and Structure-Activity Relationship Studies
  作者：Ulrike Eggert、Randi Diestel、Florenz Sasse、Rolf Jansen、Brigitte Kunze、Markus Kalesse

  DOI：10.1002/anie.200801156

  日期：2008.8.11
• Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction
  作者：Ian Paterson、Henry-Georges Lombart、Charlotte Allerton

  DOI：10.1021/ol990004c

  日期：1999.7.1

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.