tert-butyl (4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate | 215171-12-3

• 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: tert-butyl (4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 215171-12-3
• 化学式: C₂₃H₃₉NO₄Si
• 分子量: 421.652
• InChiKey: KSHYWEXDOKVHJC-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate 在 ruthenium(IV) oxide 、 sodium periodate 、 四丁基氟化铵 、 碳酸氢钠 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 多烯紫杉醇侧链杂质
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8
• 作为产物：
  描述：

  (2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol 在 咪唑 、 4-二甲氨基吡啶 、 左旋樟脑磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 14.5h， 生成 tert-butyl (4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine

  摘要：

  A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained alpha,beta-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and alpha-hydroxy-beta-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00741-8