(4R,5S)-4-allyl-3-tert-butoxycarbonyl-5-formyl-2,2-dimethyl-oxazolidine | 596108-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-4-allyl-3-tert-butoxycarbonyl-5-formyl-2,2-dimethyl-oxazolidine
• 英文别名: tert-butyl (4R,5S)-5-formyl-2,2-dimethyl-4-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 596108-93-9
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: MFRBEOCZOKAECR-GHMZBOCLSA-N

物化性质

• 沸点：
  341.4±42.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-allyl-3-tert-butoxycarbonyl-5-formyl-2,2-dimethyl-oxazolidine 、 四乙烯基锡 、 乙酸酐 在 甲基锂 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4R,5S)-5-((S)-1-acetoxyallyl)-4-allyl-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidine 、 (4R,5S)-5-((R)-1-acetoxyallyl)-4-allyl-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidine
  参考文献：
  名称：

  Stereodivergent Syntheses of Conduramines and Aminocyclitols

  摘要：

  [GRAPHICS]The diastereomers of 6-amino-cyclohex-3-ene- 1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provided a new family of aminocyclitols 2 (deoxyinosamines). The key reactions of our syntheses are Sharpless catalytic asymmetric epoxidation, diastereoselective addition of vinylmetal reagents to the aldehydes, and ring-closing metathesis (RCM).

  DOI：

  10.1021/ol061022e
• 作为产物：
  描述：

  (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-5-hexen-2-ol 在 草酰氯 、 四丁基氟化铵 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.33h， 生成 (4R,5S)-4-allyl-3-tert-butoxycarbonyl-5-formyl-2,2-dimethyl-oxazolidine
  参考文献：
  名称：

  Stereodivergent Syntheses of Conduramines and Aminocyclitols

  摘要：

  [GRAPHICS]The diastereomers of 6-amino-cyclohex-3-ene- 1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provided a new family of aminocyclitols 2 (deoxyinosamines). The key reactions of our syntheses are Sharpless catalytic asymmetric epoxidation, diastereoselective addition of vinylmetal reagents to the aldehydes, and ring-closing metathesis (RCM).

  DOI：

  10.1021/ol061022e

文献信息

• Stereodivergent Syntheses of Conduramines and Aminocyclitols
  作者：Carlos Alegret、Jordi Benet-Buchholz、Antoni Riera

  DOI：10.1021/ol061022e

  日期：2006.7.1

  [GRAPHICS]The diastereomers of 6-amino-cyclohex-3-ene- 1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provided a new family of aminocyclitols 2 (deoxyinosamines). The key reactions of our syntheses are Sharpless catalytic asymmetric epoxidation, diastereoselective addition of vinylmetal reagents to the aldehydes, and ring-closing metathesis (RCM).