(1S,2S,5S,6R)-3-benzyl-2-exo-sec-butyl-6-endo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane | 475280-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,5S,6R)-3-benzyl-2-exo-sec-butyl-6-endo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane
• 英文别名: [(1S,4S,5S,7R)-3-benzyl-4-(2-methylpropyl)-6,8-dioxa-3-azabicyclo[3.2.1]octan-7-yl]methanol
• CAS: 475280-87-6
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: LDJYYTJNQNVKGM-NXOAAHMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S,6R)-3-benzyl-2-exo-sec-butyl-6-endo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane 在 20percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以99%的产率得到(1S,2S,5S,6R)-2-exo-sec-butyl-6-endo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and Conformational Analysis of Small Peptides Containing 6-Endo-BT(t)L Scaffolds as Reverse Turn Mimetics

  摘要：

  Two new dipeptide isosteres derived from L-leucine and meso-tartaric acid derivatives, named 6-endo-BTL and 6-endo-BtL, were inserted in a small peptide by means of SPPS, and the conformational features of the resulting peptides 3 and 4 were studied by NMR, IR, and molecular modeling techniques. The presence of a reverse turn conformation was observed in all the structures, suggesting the key role of the scaffolds as reverse turn promoters. Peptides 3 and 4 did not adopt a preferred conformation as indicated by the presence of equilibria between open turn and intramolecular hydrogen-bonded structures. 6-endo-BTL-peptide 3 showed a 3:1 mixture of conformers. The major conformer adopted mainly an open turn structure in equilibrium with hydrogen-bonded structures. The minor conformer displayed a better organized structure with a 14-membered ring hydrogen-bond typical of a beta-hairpin-like structure, in equilibrium with a gamma-turn, too. 6-endo-BtL-peptide 4 showed a unique conformer, and did not adopt as good a conformation as 3, due to the bulky equatorial substituent at C-2. Thus, marked structural differences between peptides containing 6-endo-BTL and 6-endo-BtL scaffolds as reverse turn inducers exist.

  DOI：

  10.1021/jo0202132
• 作为产物：
  描述：

  (1R,4S,5S,7S)-3-Benzyl-4-isobutyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以71%的产率得到(1S,2S,5S,6R)-3-benzyl-2-exo-sec-butyl-6-endo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and Conformational Analysis of Small Peptides Containing 6-Endo-BT(t)L Scaffolds as Reverse Turn Mimetics

  摘要：

  Two new dipeptide isosteres derived from L-leucine and meso-tartaric acid derivatives, named 6-endo-BTL and 6-endo-BtL, were inserted in a small peptide by means of SPPS, and the conformational features of the resulting peptides 3 and 4 were studied by NMR, IR, and molecular modeling techniques. The presence of a reverse turn conformation was observed in all the structures, suggesting the key role of the scaffolds as reverse turn promoters. Peptides 3 and 4 did not adopt a preferred conformation as indicated by the presence of equilibria between open turn and intramolecular hydrogen-bonded structures. 6-endo-BTL-peptide 3 showed a 3:1 mixture of conformers. The major conformer adopted mainly an open turn structure in equilibrium with hydrogen-bonded structures. The minor conformer displayed a better organized structure with a 14-membered ring hydrogen-bond typical of a beta-hairpin-like structure, in equilibrium with a gamma-turn, too. 6-endo-BtL-peptide 4 showed a unique conformer, and did not adopt as good a conformation as 3, due to the bulky equatorial substituent at C-2. Thus, marked structural differences between peptides containing 6-endo-BTL and 6-endo-BtL scaffolds as reverse turn inducers exist.

  DOI：

  10.1021/jo0202132

文献信息

• Synthesis and Conformational Analysis of Small Peptides Containing 6-<i>E</i><i>ndo</i>-BT(t)L Scaffolds as Reverse Turn Mimetics
  作者：Andrea Trabocchi、Ernesto G. Occhiato、Donatella Potenza、Antonio Guarna

  DOI：10.1021/jo0202132

  日期：2002.10.1

  Two new dipeptide isosteres derived from L-leucine and meso-tartaric acid derivatives, named 6-endo-BTL and 6-endo-BtL, were inserted in a small peptide by means of SPPS, and the conformational features of the resulting peptides 3 and 4 were studied by NMR, IR, and molecular modeling techniques. The presence of a reverse turn conformation was observed in all the structures, suggesting the key role of the scaffolds as reverse turn promoters. Peptides 3 and 4 did not adopt a preferred conformation as indicated by the presence of equilibria between open turn and intramolecular hydrogen-bonded structures. 6-endo-BTL-peptide 3 showed a 3:1 mixture of conformers. The major conformer adopted mainly an open turn structure in equilibrium with hydrogen-bonded structures. The minor conformer displayed a better organized structure with a 14-membered ring hydrogen-bond typical of a beta-hairpin-like structure, in equilibrium with a gamma-turn, too. 6-endo-BtL-peptide 4 showed a unique conformer, and did not adopt as good a conformation as 3, due to the bulky equatorial substituent at C-2. Thus, marked structural differences between peptides containing 6-endo-BTL and 6-endo-BtL scaffolds as reverse turn inducers exist.