methyl (2R,3S)-5-[tert-butyl(diphenyl)silyl]oxy-2-ethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate | 122717-03-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,3S)-5-[tert-butyl(diphenyl)silyl]oxy-2-ethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 122717-03-7；122717-08-2
• 化学式: C₂₉H₄₃NO₅Si
• 分子量: 513.75
• InChiKey: KGXXHWARPDVAES-RPBOFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  methyl (2R,3S)-5-[tert-butyl(diphenyl)silyl]oxy-2-ethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-azetidin-2-one
  参考文献：
  名称：

  A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of N-Alkoxycarbonyl-1-methoxyamines with Esters

  摘要：

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.

  DOI：

  10.1021/jo990821q
• 作为产物：
  描述：

  Carbamic acid, (3-hydroxy-1-methoxypropyl)-, 1,1-dimethylethyl ester (9CI) 在 咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl (2R,3S)-5-[tert-butyl(diphenyl)silyl]oxy-2-ethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
  参考文献：
  名称：

  在将α-甲氧基氨基甲酸酯原位生成的N-甲氧基羰基亚胺中加入烯酸酯阴离子的非对映选择性

  摘要：

  研究了向α-甲氧基氨基甲酸酯原位生成的N-甲氧基羰基亚胺中添加酮或酯的烯醇酸根阴离子的非对映选择性。

  DOI：

  10.1016/s0040-4039(00)72728-6

文献信息

• Asymmetric Synthesis of <i>anti</i>-α,β-Disubstituted β-Amino Acid Derivatives by Reaction of <i>N</i>-Alkoxycarbonyl-1-methoxyamines with Optically Active 2-Oxazolidinones
  作者：Naoki Kise、Nasuo Ueda

  DOI：10.1021/ol991053s

  日期：1999.12.1

  [GRAPHICS]The reaction of N-alkoxycarbonyl-1-methoxyamines and (4S)-3-butyryl-4-isopropyl-2-oxazolidinone afforded the corresponding adducts with anti selectively (60% de). Both anti- and syn-alpha,beta-disubstituted beta amino acid methyl eaters were obtained in 98% ee from the adducts. The enantiomerically pure precursor for the synthesis of carbapenem antibiotic PS-5 was prepared by this method.
• SHONO, TATSUYA;KISE, NAOKI;SANDA, FUMIO;OHI, SATORI;YOSHIOKA, KEN, TETRAHEDRON LETT., 30,(1989) N0, C. 1253-1256
  作者：SHONO, TATSUYA、KISE, NAOKI、SANDA, FUMIO、OHI, SATORI、YOSHIOKA, KEN

  DOI：——

  日期：——
• A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of <i>N</i>-Alkoxycarbonyl-1-methoxyamines with Esters
  作者：Naoki Kise、Nasuo Ueda

  DOI：10.1021/jo990821q

  日期：1999.10.1

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.
• Diastereoselectivity in the addition of enolate anions to N-methoxycarbonylimines generated in situ from α-methoxy carbamates
  作者：Tatsuya Shono、Naoki Kise、Fumio Sanda、Satoru Ohi、Ken Yoshioka

  DOI：10.1016/s0040-4039(00)72728-6

  日期：1989.1

  The diastereoselectivity of the addition of enolate anions of ketones or esters to N-Methoxycarbonylimines generated in situ from α-Methoxy carbamates was studied.

  研究了向α-甲氧基氨基甲酸酯原位生成的N-甲氧基羰基亚胺中添加酮或酯的烯醇酸根阴离子的非对映选择性。