tert-butyl (4R,5R)-4-allyl-2-phenyl-1,3-dioxan-5-ylcarbamate | 1417141-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: tert-butyl (4R,5R)-4-allyl-2-phenyl-1,3-dioxan-5-ylcarbamate
• 英文别名: tert-butyl N-[(4R,5R)-2-phenyl-4-prop-2-enyl-1,3-dioxan-5-yl]carbamate
• CAS: 1417141-61-7
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: LMDPRVXMXCCTGS-YGFGXBMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,5R)-4-allyl-2-phenyl-1,3-dioxan-5-ylcarbamate 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到tert-butyl (2R,3R)-3-(benzyloxy)-1-hydroxyhex-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
• 作为产物：
  描述：

  在 sodium periodate 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 2,2-二甲氧基丙烷 作用下， 以 1,4-二氧六环 、 水 、 甲醇 、 丙酮 为溶剂， 反应 8.0h， 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

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.