tert-butyl (2S,3R,Z)-3-(benzyloxy)-9-hydroxynon-5-en-2-ylcarbamate | 1417141-94-6

• 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: tert-butyl (2S,3R,Z)-3-(benzyloxy)-9-hydroxynon-5-en-2-ylcarbamate
• CAS: 1417141-94-6
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: GSLJBOZGNRMJOI-LDHAIWNLSA-N

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-(benzyloxy)-9-hydroxy-1-(phenylthio)non-5-en-2-ylcarbamate 在 Raney 2800 nickel 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到
  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