tert-butyl (2S,3R)-3-(benzyloxy)-1-(phenylthio)hex-5-en-2-ylcarbamate | 1417141-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2S,3R)-3-(benzyloxy)-1-(phenylthio)hex-5-en-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S,3R)-3-phenylmethoxy-1-phenylsulfanylhex-5-en-2-yl]carbamate
• CAS: 1417141-82-2
• 化学式: C₂₄H₃₁NO₃S
• 分子量: 413.581
• InChiKey: KYHGRDVUHIHCKU-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-戊烯-1-乙酸酯 、 tert-butyl (2S,3R)-3-(benzyloxy)-1-(phenylthio)hex-5-en-2-ylcarbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium periodate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  在 aluminum (III) chloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 三丁基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 tert-butyl (2S,3R)-3-(benzyloxy)-1-(phenylthio)hex-5-en-2-ylcarbamate
  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