rhizochalinin C | 1004787-15-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rhizochalinin C
• 英文别名: rizochalinin C；(2R,3R,26R,27R)-2,27-diamino-3,26,28-trihydroxyoctacosan-11-one
• CAS: 1004787-15-8
• 化学式: C₂₈H₅₈N₂O₄
• 分子量: 486.78
• InChiKey: UPVBMGUHAOGASW-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  130
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rhizochalinin C 、 苯甲酰氯 在 吡啶 作用下， 生成 perbenzoyl oceanin
  参考文献：
  名称：

  d-Glucosamine-Derived Synthons for Assembly of l-threo-Sphingoid Bases. Total Synthesis of Rhizochalinin C

  摘要：

  A five-step transformation of D-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of L-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, "two-headed" sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.

  DOI：

  10.1021/jo302355t
• 作为产物：
  描述：

  rhizochalin C 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以0.5 mg的产率得到rhizochalinin C
  参考文献：
  名称：

  Rhizochalins C and D from the Sponge Rhizochalina incrustata. A Rare threo-Sphingolipid and a Facile Method for Determination of the Carbonyl Position in α,ω-Bifunctionalized Ketosphingolipids

  摘要：

  Rhizochalins C and D (1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C-29 homologue of the canonical C-28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.

  DOI：

  10.1021/np0704811

文献信息

• Rhizochalins C and D from the Sponge <i>Rhizochalina incrustata.</i> A Rare <i>threo</i>-Sphingolipid and a Facile Method for Determination of the Carbonyl Position in α,ω-Bifunctionalized Ketosphingolipids
  作者：Tatyana N. Makarieva、Pavel S. Dmitrenok、Alexander M. Zakharenko、Vladimir A. Denisenko、Alla G. Guzii、Ronghua Li、Colin K. Skepper、Tadeusz F. Molinski、Valentin A. Stonik

  DOI：10.1021/np0704811

  日期：2007.12.1

  Rhizochalins C and D (1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C-29 homologue of the canonical C-28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.
• <scp>d</scp>-Glucosamine-Derived Synthons for Assembly of <scp>l</scp>-<i>threo</i>-Sphingoid Bases. Total Synthesis of Rhizochalinin C
  作者：Jaeyoung Ko、Tadeusz F. Molinski

  DOI：10.1021/jo302355t

  日期：2013.1.18

  A five-step transformation of D-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of L-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, "two-headed" sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.