benzyl N-[(4R,5R)-4-[(E)-16-diethoxyphosphoryl-15-oxohexadec-2-enyl]-2,2-dimethyl-1,3-dioxan-5-yl]carbamate | 1417141-74-2

• 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: benzyl N-[(4R,5R)-4-[(E)-16-diethoxyphosphoryl-15-oxohexadec-2-enyl]-2,2-dimethyl-1,3-dioxan-5-yl]carbamate
• CAS: 1417141-74-2
• 化学式: C₃₄H₅₆NO₈P
• 分子量: 637.794
• InChiKey: VZFMRHAPVFVIKK-YCKQIAHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  44
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲基膦酸二乙酯 、 在 正丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.42h， 以81.132%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

文献信息

• <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.