(S)-3-(4-Hydroxy-phenyl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic acid | 173966-40-0

• 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: (S)-3-(4-Hydroxy-phenyl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic acid
• 英文别名: (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]propanoic acid
• CAS: 173966-40-0
• 化学式: C₂₁H₂₉NO₈
• 分子量: 423.463
• InChiKey: WULMDRYIINXSDY-SZDLEDHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115.71
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Hydroxy-phenyl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic acid 在 N-甲基吗啉 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.33h， 生成 N-(1-deoxy-D-fructos-1-yl)-L-tyrosylglycylglycyl-L-phenylalanyl-L-leucine trifluoroacetate
  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-酪氨酸 在 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以56%的产率得到(S)-3-(4-Hydroxy-phenyl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic 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