(3R,6S,7S,8S,9R,9aR)-7,8,9-Trihydroxy-5-oxo-6-trifluoromethanesulfonyloxy-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester | 452084-73-0

• 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: (3R,6S,7S,8S,9R,9aR)-7,8,9-Trihydroxy-5-oxo-6-trifluoromethanesulfonyloxy-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester
• 英文别名: methyl (3R,6S,7S,8S,9R,9aR)-7,8,9-trihydroxy-5-oxo-6-(trifluoromethylsulfonyloxy)-3,6,7,8,9,9a-hexahydro-2H-[1,3]thiazolo[3,2-a]azepine-3-carboxylate
• CAS: 452084-73-0
• 化学式: C₁₁H₁₄F₃NO₉S₂
• 分子量: 425.361
• InChiKey: NEHXSNYTMGKKGG-LZMYCMFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3R,6S,7S,8S,9R,9aR)-7,8,9-Trihydroxy-5-oxo-6-trifluoromethanesulfonyloxy-octahydro-thiazolo[3,2-a]azepine-3-carboxylic acid methyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82%的产率得到methyl (3R,6S,7R,8S,9R,9aR)-6-azido-7,8,9-trihydroxy-5-oxo-3,6,7,8,9,9a-hexahydro-2H-[1,3]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：

  三氟甲磺酸酐 、 (3R,6S,7S,8S,9R,9aR)-methyl octahydro-6,7,8,9-tetrahydroxy-5-oxothiazolo[3,2-a]azepine-3-carboxylate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到(3R,6S,7S,8S,9R,9aR)-7,8,9-Trihydroxy-5-oxo-6-trifluoromethanesulfonyloxy-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

• Synthesis of hydroxylated hexahydropyrrolo[2,1-b]thiazoles
  作者：Karoly Agoston、Armin Geyer

  DOI：10.1016/j.tetlet.2004.01.016

  日期：2004.2

  An unexpected ring contraction of 7,5-fused bicyclic thiazolidinelactams yields hexahydropyrrolo[2,1-b]thiazoles in a single synthetic step. Three stereocentres are inverted along the highly stereoselective reaction path. The title compounds are further transformed into thio-analogues of polyhydroxylated pyrrolizidine alkaloids. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.