(2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal | 909913-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal
• 英文别名: (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3-(5-phenylmethoxypyridin-2-yl)propanal
• CAS: 909913-43-5
• 化学式: C₂₂H₃₁NO₃Si
• 分子量: 385.579
• InChiKey: PTPSOSNFWRTBFH-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.33h， 生成 (2R,3S,4S)-4-[2-(5-benzyloxypyridyl)]-2-hydroxy-3-methyl-butano-4-lactone
  参考文献：
  名称：

  First chiral synthesis of the N-terminal amino acid congener of nikkomycin Z based on lipase-catalyzed enantioselective acetylation of a primary alcohol possessing two stereogenic centers

  摘要：

  A stereoselective synthesis of a versatile chiral synthon possessing two stereogenic centers, (2S,3S)-3-[2-(5-benzyloxypyridyl)]2-methyl-1,3-propane diol 12 (> 99% ee), was achieved by using a chemo-enzymatic method. The conversion of (2S,3S)-12 to the homochiral intermediate (2S,3S,4S)-2-benzyloxycarbonylamino-4-[2-(5-benzyloxypyridyl)]-4-tert-butyldimethylsilyloxy-3-methylbutanoic acid 2 corresponding to the N-terminal amino acid congener of nikkomycin Z1 is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.010
• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 在 咪唑 、 lithium aluminium tetrahydride 、 草酰氯 、 Pseudomonas sp. lipase 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 异丙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 39.17h， 生成 (2R,3S)-3-[2-(5-benzyloxypyridyl)]-3-tert-butyldimethylsilyloxy-2-methylpropanal
  参考文献：
  名称：

  First chiral synthesis of the N-terminal amino acid congener of nikkomycin Z based on lipase-catalyzed enantioselective acetylation of a primary alcohol possessing two stereogenic centers

  摘要：

  A stereoselective synthesis of a versatile chiral synthon possessing two stereogenic centers, (2S,3S)-3-[2-(5-benzyloxypyridyl)]2-methyl-1,3-propane diol 12 (> 99% ee), was achieved by using a chemo-enzymatic method. The conversion of (2S,3S)-12 to the homochiral intermediate (2S,3S,4S)-2-benzyloxycarbonylamino-4-[2-(5-benzyloxypyridyl)]-4-tert-butyldimethylsilyloxy-3-methylbutanoic acid 2 corresponding to the N-terminal amino acid congener of nikkomycin Z1 is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.010

文献信息

• First chiral synthesis of the N-terminal amino acid congener of nikkomycin Z based on lipase-catalyzed enantioselective acetylation of a primary alcohol possessing two stereogenic centers
  作者：Hiroyuki Akita、Yoshiki Takano、Katsushi Nedu、Keisuke Kato

  DOI：10.1016/j.tetasy.2006.06.010

  日期：2006.7

  A stereoselective synthesis of a versatile chiral synthon possessing two stereogenic centers, (2S,3S)-3-[2-(5-benzyloxypyridyl)]2-methyl-1,3-propane diol 12 (> 99% ee), was achieved by using a chemo-enzymatic method. The conversion of (2S,3S)-12 to the homochiral intermediate (2S,3S,4S)-2-benzyloxycarbonylamino-4-[2-(5-benzyloxypyridyl)]-4-tert-butyldimethylsilyloxy-3-methylbutanoic acid 2 corresponding to the N-terminal amino acid congener of nikkomycin Z1 is described. (c) 2006 Elsevier Ltd. All rights reserved.