N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide | 374073-04-8

• 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: N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide
• 英文别名: N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))-phenylmethoxycarboxamide；benzyl N-[(2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxooxan-3-yl]carbamate
• CAS: 374073-04-8
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: OSPMCIXSWNXBQE-YPHNTLSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2S,6S,3R,4R,5R)-4-hydroxy-3-methoxy-4,6-dimethyl-5-[(phenylmethoxy)carbonylamino]perhydro-2H-pyran-2-yl acetate
  参考文献：
  名称：

  An Aldol-Based Approach to the Asymmetric Synthesis of l-Callipeltose, the Deoxyamino Sugar of l-Callipeltoside A

  摘要：

  [GRAPHICS]The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.

  DOI：

  10.1021/ol016416e
• 作为产物：
  描述：

  N-苄氧羰基-D-苏氨酸 在 氢氟酸 、 异丙基氯化镁 、 potassium carbonate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.08h， 生成 N-((2S,3R,4R,5R)-4-hydroxy-5-methoxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide
  参考文献：
  名称：

  An Aldol-Based Approach to the Asymmetric Synthesis of l-Callipeltose, the Deoxyamino Sugar of l-Callipeltoside A

  摘要：

  [GRAPHICS]The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.

  DOI：

  10.1021/ol016416e

文献信息

• Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment
  作者：David A. Evans、Jason D. Burch、Essa Hu、Georg Jaeschke

  DOI：10.1016/j.tet.2008.02.001

  日期：2008.5

  The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments

  描述了 callipeltoside A 的对映选择性全合成。包括大环内酯亚基的两种合成：第一种依赖于爱尔兰-克莱森重排来产生三取代的烯烃几何结构，第二种利用对映选择性插烯羟醛反应来实现此目的。还公开了糖和氯代环丙烷侧链片段的对映选择性合成。该天然产物的相对和绝对立体化学通过与侧链片段的两种对映异构体的片段偶联来确定。
• An Aldol-Based Approach to the Asymmetric Synthesis of <scp>l</scp>-Callipeltose, the Deoxyamino Sugar of <scp>l</scp>-Callipeltoside A
  作者：David A. Evans、Essa Hu、Jason S. Tedrow

  DOI：10.1021/ol016416e

  日期：2001.10.1

  [GRAPHICS]The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.