27-O-diethylphosphonoacetylmyricerone | 186382-81-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 27-O-diethylphosphonoacetylmyricerone
• 英文别名: (4aS,6aR,6aR,6bR,8aR,12aR,14bS)-6a-[(2-diethoxyphosphorylacetyl)oxymethyl]-2,2,6b,9,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
• CAS: 186382-81-0
• 化学式: C₃₆H₅₇O₈P
• 分子量: 648.818
• InChiKey: VBIXWEFKEQTBME-HLTIWEOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  27-O-diethylphosphonoacetylmyricerone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (4-碘-苯甲基)-膦酸二乙基酯
  参考文献：
  名称：

  Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

  摘要：

  Myriceric acid A (1) is an oleanane triterpene that is a potent and specific endothelin A receptor antagonist. A practical procedure for large-scale synthesis of myriceric acid A (1) has been developed starting from oleanolic acid 4. The conversion of oleanolic acid 4 to the key intermediate myricerone 3 was achieved in an efficient manner employing a photochemical reaction (the Barton reaction) of nitrite 7. Our synthetic procedure alleviated several difficulties of the original Barton's procedure with regard to yields and large-scale operation. Myricerone 3 afforded Horner-Wadsworth-Emmons (HWE) type phosphonate 2 which has proved to be a versatile precursor of 1. The preparation of phosphonate 2 on a scale of several hundred grams is described. The synthesis was completed by condensation of 2 with 3,4-bis[(diphenylmethyl)oxy]benzaldehyde (21), giving alpha,beta-unsaturated ester 22, which was deprotected to afford 1. The whole synthetic sequence is efficient (14 steps, 31% yield) and requires no chromatographic purification except to obtain the final product 1.

  DOI：

  10.1021/jo9615864
• 作为产物：
  描述：

  myricerone ketal 在 盐酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 27-O-diethylphosphonoacetylmyricerone
  参考文献：
  名称：

  Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

  摘要：

  Myriceric acid A (1) is an oleanane triterpene that is a potent and specific endothelin A receptor antagonist. A practical procedure for large-scale synthesis of myriceric acid A (1) has been developed starting from oleanolic acid 4. The conversion of oleanolic acid 4 to the key intermediate myricerone 3 was achieved in an efficient manner employing a photochemical reaction (the Barton reaction) of nitrite 7. Our synthetic procedure alleviated several difficulties of the original Barton's procedure with regard to yields and large-scale operation. Myricerone 3 afforded Horner-Wadsworth-Emmons (HWE) type phosphonate 2 which has proved to be a versatile precursor of 1. The preparation of phosphonate 2 on a scale of several hundred grams is described. The synthesis was completed by condensation of 2 with 3,4-bis[(diphenylmethyl)oxy]benzaldehyde (21), giving alpha,beta-unsaturated ester 22, which was deprotected to afford 1. The whole synthetic sequence is efficient (14 steps, 31% yield) and requires no chromatographic purification except to obtain the final product 1.

  DOI：

  10.1021/jo9615864

文献信息

• Practical Large-Scale Synthesis of Endothelin Receptor Antagonist S-0139
  作者：Toshiro Konoike、Katsuo Oda、Masaaki Uenaka、Kazuhiro Takahashi

  DOI：10.1021/op990036f

  日期：1999.9.1
• Labelling of S-0139 with [M+4]-fumaric acid
  作者：Alan H. Wadsworth、Kenneth W. M. Lawrie

  DOI：10.1002/jlcr.1240

  日期：2007.4