benzyl (2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoate | 174193-56-7

• 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: benzyl (2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoate
• CAS: 174193-56-7
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: KVQXCLBXWGQJEI-BLFCVCRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙二醇甲醚 、 benzyl (2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 24.0h， 以53%的产率得到(2S)-3-(4-hydroxyphenyl)-2-[methyl-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl]amino]propanoic acid
  参考文献：
  名称：

  Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine–enkephalin

  摘要：

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).

  DOI：

  10.1039/p29960000789
• 作为产物：
  描述：

  2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 、 L-tyrosine benzyl ester 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 以60%的产率得到benzyl (2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoate
  参考文献：
  名称：

  Amadori化合物N-（2,3：4,5-二-O-异亚丙基-1-脱氧-β-d-果糖吡喃并-1-基）-1-酪氨酸苄酯的合成和构象分析

  摘要：

  摘要制备了标题化合物，该化合物是合成其他Amadori型类似物的前体，并通过X射线结构分析和NMR光谱进行了表征。在正交空间群P212121中结晶的分子，其中a = 10.441（2），b = 10.894（2），c = 24.686（4）A，Z = 4。该分子即使在固态时也具有柔韧性。在100 K时，在晶胞中存在苄氧基的两个取向。因此，分子力学和分子动力学模拟被用来研究其构象变化。将获得的结果与实验观察结果进行比较。比较分析表明，晶体中检测到的两个构象异构体与Me2SO溶液中的能量有利构象不同。关于两个CN键的旋转影响整体分子构象。被两个二氧戊环环封闭的β-d-果糖吡喃糖部分是分子中较不灵活的部分；在固态和Me2SO-d6中处于偏斜构象。

  DOI：

  10.1016/0008-6215(95)00255-3

文献信息

• Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-<scp>D</scp>-fructose derivatives) related to the opioid peptide, leucine–enkephalin
  作者：Andreja Jakas、Štefica Horvat

  DOI：10.1039/p29960000789

  日期：——

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).
• Synthesis and conformational analysis of the Amadori compound N-(2,3:4,5-di-O-isopropylidene-1-deoxy-β-d-fructopyranos-1-yl)-l-tyrosine benzyl ester
  作者：Biserka Kojić-Prodić、Vjekoslav Milinković、Jurka Kidrić、Primoẑ Pristovšek、Stefica Horvat、Andreja Jakas

  DOI：10.1016/0008-6215(95)00255-3

  日期：1995.12

  comparative analysis revealed that the two conformers detected in the crystal are different from the energetically favourable conformations in Me2SO solutions. Rotations about both C-N bonds affect the global molecular conformation. The β-d-fructopyranose moiety blocked with two dioxolane rings is the less flexible part of the molecule; in the solid state and in Me2SO-d6 it is in the skew conformation.

  摘要制备了标题化合物，该化合物是合成其他Amadori型类似物的前体，并通过X射线结构分析和NMR光谱进行了表征。在正交空间群P212121中结晶的分子，其中a = 10.441（2），b = 10.894（2），c = 24.686（4）A，Z = 4。该分子即使在固态时也具有柔韧性。在100 K时，在晶胞中存在苄氧基的两个取向。因此，分子力学和分子动力学模拟被用来研究其构象变化。将获得的结果与实验观察结果进行比较。比较分析表明，晶体中检测到的两个构象异构体与Me2SO溶液中的能量有利构象不同。关于两个CN键的旋转影响整体分子构象。被两个二氧戊环环封闭的β-d-果糖吡喃糖部分是分子中较不灵活的部分；在固态和Me2SO-d6中处于偏斜构象。