α-tert-butyl γ-methyl N-trityl-L-glutamate | 118545-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: α-tert-butyl γ-methyl N-trityl-L-glutamate
• 英文别名: α-t-butyl γ-methyl N-trityl-(S)-glutamate；α-t-butyl γ-methyl N-trityl-L-glutamate；1-O-tert-butyl 5-O-methyl (2S)-2-(tritylamino)pentanedioate
• CAS: 118545-50-9
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: ASOFJVWJLNNBMC-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  丙醛 、 α-tert-butyl γ-methyl N-trityl-L-glutamate 在 lithium cyclohexylisopropylamide 作用下， 以 正己烷 为溶剂， 以68%的产率得到t-butyl 2-tritylamino-4-carbomethoxy-5-hydroxy-(2S)-heptanoate
  参考文献：
  名称：

  立体特异性氨基酸合成；谷氨酸衍生的γ-阴离子的制备

  摘要：

  α-叔丁基γ-甲基N-三苯甲基-L-谷氨酸盐（7）与异丙基环己基锂锂在己烷中的反应导致γ-酯烯醇化物的特定形成，这是立体定向α的γ-阴离子合成子的潜在合成等价物-氨基酸合成。

  DOI：

  10.1039/c39880000828
• 作为产物：
  描述：

  L-谷氨酸-5-甲酯 在 硫酸 、 三乙胺 作用下， 生成 α-tert-butyl γ-methyl N-trityl-L-glutamate
  参考文献：
  名称：

  立体特异性氨基酸合成；谷氨酸衍生的γ-阴离子的制备

  摘要：

  α-叔丁基γ-甲基N-三苯甲基-L-谷氨酸盐（7）与异丙基环己基锂锂在己烷中的反应导致γ-酯烯醇化物的特定形成，这是立体定向α的γ-阴离子合成子的潜在合成等价物-氨基酸合成。

  DOI：

  10.1039/c39880000828

文献信息

• Synthesis of nonproteinogenic amino acids part 2: preparation of a synthetic equivalent of the γ anion synthon for asymmetric amino acid synthesis
  作者：Jack E. Baldwin、Michael North、Anthony Flinn、Mark G. Moloney

  DOI：10.1016/0040-4020(89)80144-9

  日期：1989.1

  The synthesis of α--butyl γ-methyl -trityl-(S)-glutamate (12) from (S)-glutamic acid (6) is described. Diester (12), on treatment with lithium Isopropylcyclohexylamide followed by the addition of carbonyl compounds, reacts to give the γ-substituted glutamic acid derivatives (13a-i) with retention of optical purity at the α centre.

  描述了由（S）-谷氨酸（6）合成α--丁基γ-甲基-三苯甲基-（S）-谷氨酸（12）。在用异丙基环己基氨基锂处理，然后加入羰基化合物的情况下，二酯（12）反应生成γ-取代的谷氨酸衍生物（13a-i），并在α中心保留了光学纯度。
• Synthesis of nonproteinogenic amino acids part 3: conversion of glutamic acid into γ,δ-unsaturated α-amino acids
  作者：Jack E. Baldwin、Michael North、Anthony Flinn、Mark G. Moloney

  DOI：10.1016/0040-4020(89)80145-0

  日期：1989.1

  A general procedure for the asymmetric synthesis of γ,δ-unsaturated α-amino acids (7) from the γ-anion derived from ()-glutamic acid is described.

  描述了从（- ）-谷氨酸衍生的γ-阴离子不对称合成γ，δ-不饱和α-氨基酸（7）的一般程序。
• Folate-Based Inhibitors of Thymidylate Synthase:  Synthesis and Antitumor Activity of γ-Linked Sterically Hindered Dipeptide Analogues of 2-Desamino-2-methyl-<i>N</i>¹⁰-propargyl-5,8-dideazafolic Acid (ICI 198583)
  作者：Vassilios Bavetsias、Ann L. Jackman、Jonathan H. Marriott、Rosemary Kimbell、William Gibson、F. Thomas Boyle、Graham M. F. Bisset

  DOI：10.1021/jm960878u

  日期：1997.5.1

  In an effort to synthesize inhibitors of thymidylate synthase (TS) that do not undergo polyglutamation, a series of gamma-linked sterically hindered dipeptide analogues of 2-desamino-2-methyl-N-10-propargyl-5 ,8-dideazafolic acid (ICI 198583) was prepared. A methyl, ethyl, or propargyl group was incorporated into the gamma-glutamyl amide bond of gamma-linked L,L dipeptide derivatives of ICI 198583, such as ICI 198583-gamma-L-Glu. In addition, steric bulk was introduced on either side of the gamma-glutamyl bond of ICI 198583-gamma-L-Glu or ICI 198583-gamma-L-Ala. The resulting dipeptide analogues, e.g., ICI 198583-gamma-MeGlu and ICI 198583-gamma-Aib, were apparently stable to in vivo hydrolysis but poorer inhibitors of TS and L1210 cell growth. However, introduction of 7-Me, 2'-F substitution into the quinazoline nucleus gave significant improvement in the inhibitory activity against thymidylate synthase. Compounds 28-30, the 7-Me, 2'-F derivatives of ICI 198583-gamma-MeGlu, ICI 198583-gamma-EtGlu, and ICI 198583-gamma-PgGlu, respectively, were potent inhibitors of TS (Ki(iapp) = 0.21-1.1 nM) and L1210 cell growth (IC50 = 0.05-0.34 mu M) and were similar to that seen with the most potent gamma-linked L,D dipeptide derivatives of ICI 198583 previously synthesized. Furthermore, the low cross-resistance ratios for the L1210:R-D1694/L1210 cell line indicated that 28-30 do not undergo polyglutamation.
• BALDWIN, JACK E.;NORTH, MICHAEL;FLINN, ANTHONY;MOLONEY, MARK G., TETRAHEDRON, 45,(1989) N, C. 1453-1464
  作者：BALDWIN, JACK E.、NORTH, MICHAEL、FLINN, ANTHONY、MOLONEY, MARK G.

  DOI：——

  日期：——
• BALDWIN, JACK E.;NORTH, MICHAEL;FLINN, ANTHONY;MOLONEY, MARK G., TETRAHEDRON, 45,(1989) N, C. 1465-1474
  作者：BALDWIN, JACK E.、NORTH, MICHAEL、FLINN, ANTHONY、MOLONEY, MARK G.

  DOI：——

  日期：——