2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester | 404890-45-5

• 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: 2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester
• 英文别名: benzyl 2-methyl-2-[(2R,6S)-6-(2-oxopropyl)oxan-2-yl]propanoate
• CAS: 404890-45-5
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: ZWIIWPYWXOKACO-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester 在 camphor-10-sulfonic acid 、 三乙胺 、 diethylboron trifluoromethanesulfonate 作用下， 以 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2-((2R,6S)-6-{(4S,6R)-6-[(S)-3-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u
• 作为产物：
  描述：

  2-甲酰基-2-甲基丙酸苄酯 在 Grubbs catalyst first generation 、 nickel dichloride 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 N,N-二异丙基乙胺 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.17h， 生成 2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u

文献信息

• Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448
  作者：Ashoke Bhattacharjee、Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol016938u

  日期：2002.2.1

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.