[(1S,4S,5R,8R,13R,14R,16S,17S,18R)-4,5,9,9,13,20,20-heptamethyl-10,23-dioxo-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-16-yl] nitrite | 173554-39-7

• 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: [(1S,4S,5R,8R,13R,14R,16S,17S,18R)-4,5,9,9,13,20,20-heptamethyl-10,23-dioxo-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-16-yl] nitrite
• CAS: 173554-39-7
• 化学式: C₃₀H₄₅NO₅
• 分子量: 499.691
• InChiKey: YAXADSGBFWXHEH-SPNPCYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S,4S,5R,8R,13R,14R,16S,17S,18R)-4,5,9,9,13,20,20-heptamethyl-10,23-dioxo-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-16-yl] nitrite 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以61%的产率得到C₃₀H₄₅NO₅
  参考文献：
  名称：

  Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A

  摘要：

  The Barton reaction (nitrite photolysis) of a steroidal substrate 1, to give 2, a key intermediate for the synthesis of myriceric acid A, an endothelin receptor antagonist, was successfully carried out in a continuous microflow system using a Pyrex glass-covered stainless-steel microreactor having a one lane microchannel (Type A: 1000 mu m width, 107 mu m depth, 2.2 m length). We found that using a low-power black light (peak wavelength: 352 nm) and UV-LED light (peak wavelength: 365 nm) as the light source will suffice for the Barton reaction, creating a compact energy-saving photo-microreaction system. A multi-gram-scale production was attained using a multi-lane microreactor (Type B: 1000 mu m width, 500 mu m depth, 0.5 m length, 16 lanes) in conjunction with a black light. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.063
• 作为产物：
  描述：

  3-oxo-olean-12α-hydroxy-28-oic acid γ-lactone 在 亚硝酰氯 作用下， 生成 [(1S,4S,5R,8R,13R,14R,16S,17S,18R)-4,5,9,9,13,20,20-heptamethyl-10,23-dioxo-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-16-yl] nitrite
  参考文献：
  名称：

  Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A

  摘要：

  The Barton reaction (nitrite photolysis) of a steroidal substrate 1, to give 2, a key intermediate for the synthesis of myriceric acid A, an endothelin receptor antagonist, was successfully carried out in a continuous microflow system using a Pyrex glass-covered stainless-steel microreactor having a one lane microchannel (Type A: 1000 mu m width, 107 mu m depth, 2.2 m length). We found that using a low-power black light (peak wavelength: 352 nm) and UV-LED light (peak wavelength: 365 nm) as the light source will suffice for the Barton reaction, creating a compact energy-saving photo-microreaction system. A multi-gram-scale production was attained using a multi-lane microreactor (Type B: 1000 mu m width, 500 mu m depth, 0.5 m length, 16 lanes) in conjunction with a black light. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.063

文献信息

• Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid
  作者：Toshiro Konoike、Kazuhiro Takahashi、Yoshitaka Araki、Isao Horibe

  DOI：10.1021/jo9615864

  日期：1997.2.1

  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.