(2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate | 236401-60-8

• 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: (2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate
• 英文别名: [(2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl] benzoate
• CAS: 236401-60-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: UXYLXGCDEQINPV-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate 在 sodium tetrahydroborate 、 sodium periodate 、 三氟甲磺酸 、 氯代二环己基硼烷 、 potassium carbonate 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 甲醇 、 乙醚 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 49.0h， 生成 (2S,3S,4R,5R,6S,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-octandiol
  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：

  乙醛 、 (2S)-2-(苯甲酰基氧基)-3-戊酮 在 二甲基十二/十四烷基叔胺 、 氯代二环己基硼烷 作用下， 以 乙醚 为溶剂， 反应 17.5h， 以96%的产率得到(2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate
  参考文献：
  名称：

  天奇霉素A全功能化无环核心的立体选择性合成

  摘要：

  描述了一种针对大环内酯聚酮化合物天奇霉素 A 的高度收敛的合成方法。我们合成方法的显着特点包括高度立体选择性的迈尔斯烷基化、底物控制的抗羟醛反应和 Masamune-Roush 烯化。

  DOI：

  10.24820/ark.5550190.p010.287

文献信息

• 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.
• 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.
• Stereoselective synthesis of fully functionalized acyclic core of Tianchimycin A
  作者：Yamini Vanipenta、Subhash Ghosh

  DOI：10.24820/ark.5550190.p010.287

  日期：——

  A highly convergent synthetic approach towards the macrolactone polyketide tianchimycin A is described. Notable features of our synthetic approach include highly stereoselective Myers alkylation, substrate controlled anti aldol reaction, and Masamune-Roush olefination.

  描述了一种针对大环内酯聚酮化合物天奇霉素 A 的高度收敛的合成方法。我们合成方法的显着特点包括高度立体选择性的迈尔斯烷基化、底物控制的抗羟醛反应和 Masamune-Roush 烯化。