(S)-16-[(4S,5S)-2,2-Dimethyl-5-((S)-2-methyl-decyl)-[1,3]dioxolan-4-yl]-14-hydroxy-hexadecanoic acid methyl ester | 651032-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-16-[(4S,5S)-2,2-Dimethyl-5-((S)-2-methyl-decyl)-[1,3]dioxolan-4-yl]-14-hydroxy-hexadecanoic acid methyl ester
• 英文别名: methyl (14S)-16-[(4S,5S)-2,2-dimethyl-5-[(2S)-2-methyldecyl]-1,3-dioxolan-4-yl]-14-hydroxyhexadecanoate
• CAS: 651032-56-3
• 化学式: C₃₃H₆₄O₅
• 分子量: 540.868
• InChiKey: DRVJMTWRYKLCPU-ORYMTKCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  38
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (S)-16-[(4S,5S)-2,2-Dimethyl-5-((S)-2-methyl-decyl)-[1,3]dioxolan-4-yl]-14-hydroxy-hexadecanoic acid methyl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-16-[(4S,5S)-2,2-Dimethyl-5-((S)-2-methyl-decyl)-[1,3]dioxolan-4-yl]-14-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexadecanoic acid methyl ester
  参考文献：
  名称：

  Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei¹

  摘要：

  Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C-28 fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC50 values of 48-170 nM.

  DOI：

  10.1021/ja037368r
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 (14S,17S,18S,20S)-14,17,18-Trihydroxy-20-methyl-octacosanoic acid methyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-16-[(4S,5S)-2,2-Dimethyl-5-((S)-2-methyl-decyl)-[1,3]dioxolan-4-yl]-14-hydroxy-hexadecanoic acid methyl ester
  参考文献：
  名称：

  Schulzeines A−C, New α-Glucosidase Inhibitors from the Marine Sponge Penares schulzei¹

  摘要：

  Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C-28 fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC50 values of 48-170 nM.

  DOI：

  10.1021/ja037368r