methyl (2R,3S)-2,3-dihydroxy-2,3-di-O-isopropylidene-3-(4-methylphenyl)propionate | 351340-32-4

• 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: methyl (2R,3S)-2,3-dihydroxy-2,3-di-O-isopropylidene-3-(4-methylphenyl)propionate
• 英文别名: methyl (4R,5S)-2,2-dimethyl-5-(4-methylphenyl)-1,3-dioxolane-4-carboxylate
• CAS: 351340-32-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: CPCHNBXIFZBCGC-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2,3-dihydroxy-2,3-di-O-isopropylidene-3-(4-methylphenyl)propionate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (4R,5S)-2,2-dimethyl-5-(4-methylphenyl)-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c
• 作为产物：
  描述：

  对甲基肉桂酸甲酯 在 甲基磺酰胺 、 potassium carbonate potassium dioxotetrahydroxoosmate(VI) 、 (DHQ)2-PHAL 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 1.0h， 生成 methyl (2R,3S)-2,3-dihydroxy-2,3-di-O-isopropylidene-3-(4-methylphenyl)propionate
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c