Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester | 175848-39-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
• CAS: 175848-39-2
• 化学式: C₁₁H₁₅F₃O₈S
• 分子量: 364.297
• InChiKey: FREWXABZACNBBK-TVNFTVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 钯 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 氢气 、 sodium acetate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R,3a'R,6'S,7'S,7a'R)-7'-hydroxy-2',2',6'-trimethyltetrahydrospiro[piperazine-2,4'-[1,3]dioxolo[4,5-c]pyran]-3,6-dione
  参考文献：
  名称：

  Mimics of l-rhamnose: Analogues of rhamnopyranose containing a constituent α-amino acid at the anomeric position. A rhamnopyranose analogue of hydantocidin

  摘要：

  Ionic brominative oxidation of 2-amino derivatives of protected heptonolactones derived from L-rhamnose provides a key bicyclic intermediate for the synthesis of analogues of L-rhamnopyranose with spirohydantoins and spirodiketopiperazines at the anomeric position; the same intermediate can be used for the synthesis of novel glycopeptides containing a constituent rhamnopyranose amino acid. Such materials may allow an approach to new studies of diseases induced by mycobacteria, such as tuberculosis and leprosy.

  DOI：

  10.1016/0957-4166(96)00014-6
• 作为产物：
  描述：

  三氟甲磺酸酐 、 7-deoxy-3,4-O-isopropylidene-L-glycero-L-talo-heptono-1,5-lactone 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Trifluoro-methanesulfonic acid (3aS,4S,7R,7aR)-4-((S)-1-hydroxy-ethyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  Mimics ofl-rhamnose: Synthesis of C-glycosides of L-rhamnofuranose and an α-azidoester as divergent intermediates for combinatorial generation of rhamnofuranose libraries

  摘要：

  The ring contraction of readily available delta-lactones provides a short route to the synthesis of both epimers of C-L-rhamnofuranosides, radical bromination of which give access to an alpha-azidocarboxylate as a divergent intermediate for applying combinatorial methodology for the preparation of a wide range of mimics of L-rhamnofuranose; such materials may provide an approach to the study of the biosynthesis of the cells walls of mycobacteria such as Mycobacterium tuberculosis and M. leprae.

  DOI：

  10.1016/0957-4166(96)00012-2