Onchitriol I | 140924-47-6

• 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: Onchitriol I
• 英文别名: 2-[(E,2R,3R,4R,5R,8S)-3,5-dihydroxy-8-[6-[(2S,3S)-3-hydroxypentan-2-yl]-3,5-dimethyl-4-oxopyran-2-yl]-4,6-dimethylnon-6-en-2-yl]-6-ethyl-3,5-dimethylpyran-4-one
• CAS: 140924-47-6
• 化学式: C₃₂H₄₈O₇
• 分子量: 544.729
• InChiKey: HLJUWPYOKLNZAF-UFUJGQGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-(+)-alpha-甲氧基苯乙酸 、 Onchitriol I 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 onchitriol I (S)-3,13,15-tris(O-methylmandelate)
  参考文献：
  名称：

  The natural polypropionate-derived esters of the mollusk Onchidium sp

  摘要：

  Eight new polypropionate-derived esters (5-8 and 10-13) have been isolated from pulmonate molluscs of the genus Onchidium collected in the South Pacific. The structures of these compounds were determined spectroscopically in particular by one- and two-dimensional NMR and low and high EIMS. The absolute of the seven asymmetric centers was determined by using the Trost-Mosher methodology. Saponification afforded two triols named onchitriol I and II (4 and 9, respectively). Compounds 4-13 displayed in vitro antitumor activity against several cell lines. Onchitriol I and II had antiviral activity also.

  DOI：

  10.1021/jo00043a018
• 作为产物：
  描述：

  Acetic acid (E)-(1R,4S)-1-[(1R,2R,3R)-2-benzyloxy-3-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-1-methyl-butyl]-4-{3,5-dimethyl-6-[(1S,2S)-1-methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-butyl]-4-oxo-4H-pyran-2-yl}-2-methyl-pent-2-enyl ester 在 potassium carbonate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 Onchitriol I
  参考文献：
  名称：

  完全取代的含γ-吡喃酮的天然产物的合成研究：甲壳三酚II的首次全合成

  摘要：

  描述了甲壳三醇II（一种软体动物Onchidium sp。的细胞毒性代谢产物）的第一个全合成。它采用温和的环化方法[DMSO-（COCl）2或Ph 3 P-CCl 4 ]，将带有光学活性官能团的三酮化合物与相应的γ-吡喃酮类化合物结合在一起，作为关键步骤。一些非对映异构体的额外合成提供了修改紧密相关的甲壳三酚I结构的可能性。

  DOI：

  10.1016/0040-4039(94)88516-8

文献信息

• Synthetic studies on fully substituted γ-pyrone-containing natural products: The first total synthesis of onchitriol II
  作者：Hirokazu Arimoto、Shigeru Nishiyama、Shosuke Yamamura

  DOI：10.1016/0040-4039(94)88516-8

  日期：1994.12

  The first total synthesis of onchitriol II, a cytotoxic metabolite of mollusc Onchidium sp., is described. It employs mild cyclization method [DMSO - (COCl)2 or Ph3P - CCl4] of triketides bearing optically active functional groups to the corresponding γ-pyrones as a key step. Additional synthesis of some diastereoisomers provided a possibility to revise the structure of closely related onchitriol I.

  描述了甲壳三醇II（一种软体动物Onchidium sp。的细胞毒性代谢产物）的第一个全合成。它采用温和的环化方法[DMSO-（COCl）2或Ph 3 P-CCl 4 ]，将带有光学活性官能团的三酮化合物与相应的γ-吡喃酮类化合物结合在一起，作为关键步骤。一些非对映异构体的额外合成提供了修改紧密相关的甲壳三酚I结构的可能性。
• The natural polypropionate-derived esters of the mollusk Onchidium sp
  作者：Jaime Rodriguez、Ricardo Riguera、Cecile Debitus

  DOI：10.1021/jo00043a018

  日期：1992.8

  Eight new polypropionate-derived esters (5-8 and 10-13) have been isolated from pulmonate molluscs of the genus Onchidium collected in the South Pacific. The structures of these compounds were determined spectroscopically in particular by one- and two-dimensional NMR and low and high EIMS. The absolute of the seven asymmetric centers was determined by using the Trost-Mosher methodology. Saponification afforded two triols named onchitriol I and II (4 and 9, respectively). Compounds 4-13 displayed in vitro antitumor activity against several cell lines. Onchitriol I and II had antiviral activity also.