(R)-2-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hydroxy-isoxazolidine-3-carboxylic acid ethyl ester | 256949-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hydroxy-isoxazolidine-3-carboxylic acid ethyl ester
• CAS: 256949-53-8
• 化学式: C₃₀H₄₁NO₈Si
• 分子量: 571.743
• InChiKey: FLYUBBJLBDQKRQ-MPCQMJCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hydroxy-isoxazolidine-3-carboxylic acid ethyl ester 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以100.8 mg的产率得到(3R)-2-(5'-O-tert-butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonylisoxazolidin-5-one
  参考文献：
  名称：

  Homochiral α-d- and β-d-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition

  摘要：

  The introduction of chiral auxiliaries at the C- or N-atom in starting nitrones has been investigated as a stereoselective synthetic route to heterocyclic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowing an easy and enantioselective synthesis of isoxazolidinyl thymine 26.

  DOI：

  10.1021/jo990576a
• 作为产物：
  描述：

  (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 在 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 (R)-2-[(3aR,4R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-5-hydroxy-isoxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Homochiral α-d- and β-d-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition

  摘要：

  The introduction of chiral auxiliaries at the C- or N-atom in starting nitrones has been investigated as a stereoselective synthetic route to heterocyclic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowing an easy and enantioselective synthesis of isoxazolidinyl thymine 26.

  DOI：

  10.1021/jo990576a