[(3S,4R,5R)-5-((E)-Hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-2-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester | 1053312-53-0

• 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,4R,5R)-5-((E)-Hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-2-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S,4R,5R)-5-[(E)-hexadec-2-enyl]-4-hydroxy-3-(hydroxymethyl)-2-oxooxolan-3-yl]carbamate
• CAS: 1053312-53-0
• 化学式: C₂₆H₄₇NO₆
• 分子量: 469.662
• InChiKey: NMYMHFOWAVAKAN-LLJPPCLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S,4R,5R)-5-((E)-Hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-2-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester 在 咪唑 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 [(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((E)-hexadec-2-enyl)-2,4-dioxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols

  摘要：

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.

  DOI：

  10.1021/jm960391l
• 作为产物：
  描述：

  14-deoxomyriocin 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 [(3S,4R,5R)-5-((E)-Hexadec-2-enyl)-4-hydroxy-3-hydroxymethyl-2-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols

  摘要：

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.

  DOI：

  10.1021/jm960391l

文献信息

• Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols
  作者：Tetsuro Fujita、Ryoji Hirose、Masahiko Yoneta、Shigeo Sasaki、Kenichiro Inoue、Masatoshi Kiuchi、Susumu Hirase、Kenji Chiba、Hiroshi Sakamoto、Masafumi Arita

  DOI：10.1021/jm960391l

  日期：1996.1.1

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.