(3S)-3-benzyloxycarbonylamino-4-hydroxy-5-phenyltetrahydrofuran-2-one | 1308311-61-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-3-benzyloxycarbonylamino-4-hydroxy-5-phenyltetrahydrofuran-2-one
• 英文别名: benzyl N-[(3S,4S,5S)-4-hydroxy-2-oxo-5-phenyloxolan-3-yl]carbamate
• CAS: 1308311-61-6
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: YHLIWUUTXZJXHX-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  -2-<(benzyloxycarbonyl)amino>-4-phenyl-3-butenoic acid methyl ester 在 potassium osmate(VI) dihydrate 、 N-甲基吗啉氧化物 、 hydroquinidine (anthraquinone-1,4-diyl) diether 作用下， 以 氯仿 、 水 为溶剂， 反应 16.33h， 生成 (3S)-3-benzyloxycarbonylamino-4-hydroxy-5-phenyltetrahydrofuran-2-one 、 (3S)-3-benzyloxycarbonylamino-4-hydroxy-5-phenyltetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of β,γ-Dihydroxyhomotyrosines by a Tandem Petasis–Asymmetric Dihydroxylation Approach

  摘要：

  Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' component, proceed with high stereoselectivity to produce beta,gamma-dehydrohomoarylalanine derivatives. Subsequent asymmetric dihydroxylation under neutral conditions gives the corresponding protected beta,gamma-dihydroxyhomoarylalanines with up to 15:1 dr. The method has been exploited in the efficient, stereoselective synthesis of protected beta,gamma-dihydroxyhomotyrosine, a component of the antifungal cyclic peptide echinocandin B.

  DOI：

  10.1021/ol200917s

文献信息

• Synthesis of β,γ-Dihydroxyhomotyrosines by a Tandem Petasis–Asymmetric Dihydroxylation Approach
  作者：Quentin I. Churches、Jonathan M. White、Craig A. Hutton

  DOI：10.1021/ol200917s

  日期：2011.6.3

  Petasis reactions of substituted styrenylboronic acids and glyoxylic acid, employing tert-butylsulfinamide as the 'amine' component, proceed with high stereoselectivity to produce beta,gamma-dehydrohomoarylalanine derivatives. Subsequent asymmetric dihydroxylation under neutral conditions gives the corresponding protected beta,gamma-dihydroxyhomoarylalanines with up to 15:1 dr. The method has been exploited in the efficient, stereoselective synthesis of protected beta,gamma-dihydroxyhomotyrosine, a component of the antifungal cyclic peptide echinocandin B.