tert-butyl (2R,3R)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoate | 1361343-23-8

• 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: tert-butyl (2R,3R)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoate
• 英文别名: tert-butyl (2R,3R)-5-[tert-butyl(diphenyl)silyl]oxy-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 1361343-23-8
• 化学式: C₃₁H₄₇NO₅Si
• 分子量: 541.803
• InChiKey: AIFMOGYNFTYYOY-ZEQKJWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 以95%的产率得到(2R,3R)-2-amino-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoic acid
  参考文献：
  名称：

  An Asymmetric Synthesis of l-Pyrrolysine

  摘要：

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

  DOI：

  10.1021/ol300045c
• 作为产物：
  描述：

  (3R,4R)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-3-methyl-5-oxopentanoic acid 在 N-乙基吗啉 、 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 tert-butyl (2R,3R)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)-3-methylpentanoate
  参考文献：
  名称：

  An Asymmetric Synthesis of l-Pyrrolysine

  摘要：

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

  DOI：

  10.1021/ol300045c

文献信息

• An Asymmetric Synthesis of <scp>l</scp>-Pyrrolysine
  作者：Margaret L. Wong、Ilia A. Guzei、Laura L. Kiessling

  DOI：10.1021/ol300045c

  日期：2012.3.16

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.