(3R,6S,7R,8S,9R,9aR)-6-Amino-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester | 452084-78-5

• 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: (3R,6S,7R,8S,9R,9aR)-6-Amino-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester
• 英文别名: methyl (3R,6S,7R,8S,9R,9aR)-6-amino-7,8,9-trihydroxy-5-oxo-3,6,7,8,9,9a-hexahydro-2H-[1,3]thiazolo[3,2-a]azepine-3-carboxylate
• CAS: 452084-78-5
• 化学式: C₁₀H₁₆N₂O₆S
• 分子量: 292.313
• InChiKey: NKLHXZFYCPQUNS-FQIRZYDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,6S,7R,8S,9R,9aR)-6-Amino-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester 在 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.42h， 生成 Lithium; (3R,6S,7R,8S,9R,9aR)-6-tert-butoxycarbonylamino-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepine-3-carboxylate
  参考文献：
  名称：

  An Oligomeric Ser-Pro Dipeptide Mimetic Assuming the Polyproline II Helix Conformation

  摘要：

  A hexapeptide assembled from dipeptide building blocks assumes the secondary structure of the polyproline II (PPII) helix. Side chain-to-backbone hydrogen bonds stabilize peptide torsions next to the fused ring systems. The solution structure of the polyhydroxylated peptide was studied by spectroscopic methods.

  DOI：

  10.1021/ja026098u
• 作为产物：
  描述：

  (3R,6S,7S,8S,9R,9aR)-methyl octahydro-6,7,8,9-tetrahydroxy-5-oxothiazolo[3,2-a]azepine-3-carboxylate 在 吡啶 、 sodium azide 、 硫化氢 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 (3R,6S,7R,8S,9R,9aR)-6-Amino-7,8,9-trihydroxy-5-oxo-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  An Oligomeric Ser-Pro Dipeptide Mimetic Assuming the Polyproline II Helix Conformation

  摘要：

  A hexapeptide assembled from dipeptide building blocks assumes the secondary structure of the polyproline II (PPII) helix. Side chain-to-backbone hydrogen bonds stabilize peptide torsions next to the fused ring systems. The solution structure of the polyhydroxylated peptide was studied by spectroscopic methods.

  DOI：

  10.1021/ja026098u

文献信息

• An Oligomeric Ser-Pro Dipeptide Mimetic Assuming the Polyproline II Helix Conformation
  作者：Peter Tremmel、Armin Geyer

  DOI：10.1021/ja026098u

  日期：2002.7.1

  A hexapeptide assembled from dipeptide building blocks assumes the secondary structure of the polyproline II (PPII) helix. Side chain-to-backbone hydrogen bonds stabilize peptide torsions next to the fused ring systems. The solution structure of the polyhydroxylated peptide was studied by spectroscopic methods.