benzyl (4R,5S)-4-[(1R)-1-hydroxy-1-[(2R)-3-oxo-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate | 374073-08-2

• 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 (4R,5S)-4-[(1R)-1-hydroxy-1-[(2R)-3-oxo-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 374073-08-2
• 化学式: C₂₄H₃₃NO₇
• 分子量: 447.529
• InChiKey: CAYXKFWNRZNHEF-QYUDBREXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (4R,5S)-4-[(1R)-1-hydroxy-1-[(2R)-3-oxo-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 16.0h， 以71%的产率得到N-((2S,3R,4R,5R)-4,5-dihydroxy-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
• 作为产物：
  描述：

  N-苄氧羰基-D-苏氨酸 在 正丁基锂 、 异丙基氯化镁 、 potassium carbonate 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 14.33h， 生成 benzyl (4R,5S)-4-[(1R)-1-hydroxy-1-[(2R)-3-oxo-1,4-dioxaspiro[4.5]decan-2-yl]ethyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
  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

• 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.