(3R,4R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-6-methyl-heptan-2-one | 428452-80-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-6-methyl-heptan-2-one
• 英文别名: (3R,4R)-4-azido-3-[tert-butyl(dimethyl)silyl]oxy-1-diazo-6-methylheptan-2-one
• CAS: 428452-80-6
• 化学式: C₁₄H₂₇N₅O₂Si
• 分子量: 325.486
• InChiKey: GRCGQCBBILZKOT-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-6-methyl-heptan-2-one 在 silver(I) acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 以70%的产率得到(3S,4R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoic acid
  参考文献：
  名称：

  Unusual Regioselection in the Mitsunobu Reactions of syn-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer

  摘要：

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.

  DOI：

  10.1021/jo015967f
• 作为产物：
  描述：

  (2R,3R)-3-Azido-2-hydroxy-5-methyl-hexanoic acid ethyl ester 在 咪唑 、 lithium hydroxide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4R)-4-Azido-3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-6-methyl-heptan-2-one
  参考文献：
  名称：

  Unusual Regioselection in the Mitsunobu Reactions of syn-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer

  摘要：

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.

  DOI：

  10.1021/jo015967f

文献信息

• Unusual Regioselection in the Mitsunobu Reactions of <i>s</i><i>yn</i>-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer
  作者：Soo Y. Ko

  DOI：10.1021/jo015967f

  日期：2002.4.1

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.