2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetic acid | 1135007-64-5

• 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: 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetic acid
• CAS: 1135007-64-5
• 化学式: C₃₆H₅₀N₂O₁₅
• 分子量: 750.797
• InChiKey: LQWQXLJMVOFAEY-ZTUVDBAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  53
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  197
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-4-amino-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetate 、 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以150 mg的产率得到methyl 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetate
  参考文献：
  名称：

  Synthesis and Solution Conformation of Homo-β-peptides Consisting of N-Mannofuranosyl-3-ulosonic acids

  摘要：

  The synthesis and solution conformation of homo-oligomers of beta-aminoacids, O-N-mannofuranosyl-3-ulosonic acids, have been studied by NMR, MD simulation, and circular dichroism. These oligomers feature a spirocyclic disubstitution and a N,O-acetal functionality at the P-carbon of the backbone, an unprecedented situation in the realm of beta-peptides. Our study shows that tetramer 10 and hexamer 11 adopt a characteristic secondary structure. In the hexamer 11, NMR investigations coupled with MD simulations suggest the preference for a double C-8 turn forming conformation.

  DOI：

  10.1021/jo900966b
• 作为产物：
  描述：

  methyl 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 2-[(3aS,4S,6R,6aS)-4-[[2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-(phenylmethoxycarbonylamino)-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetyl]amino]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetic acid
  参考文献：
  名称：

  Synthesis and Solution Conformation of Homo-β-peptides Consisting of N-Mannofuranosyl-3-ulosonic acids

  摘要：

  The synthesis and solution conformation of homo-oligomers of beta-aminoacids, O-N-mannofuranosyl-3-ulosonic acids, have been studied by NMR, MD simulation, and circular dichroism. These oligomers feature a spirocyclic disubstitution and a N,O-acetal functionality at the P-carbon of the backbone, an unprecedented situation in the realm of beta-peptides. Our study shows that tetramer 10 and hexamer 11 adopt a characteristic secondary structure. In the hexamer 11, NMR investigations coupled with MD simulations suggest the preference for a double C-8 turn forming conformation.

  DOI：

  10.1021/jo900966b