7-deoxy-3,4-O-isopropylidene-L-glycero-L-talo-heptono-1,5-lactone | 161721-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 7-deoxy-3,4-O-isopropylidene-L-glycero-L-talo-heptono-1,5-lactone
• 英文别名: (3aS,4S,7R,7aS)-7-hydroxy-4-[(1S)-1-hydroxyethyl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 161721-48-8
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: RHHLZBSICPQIHL-GWVFRZDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-deoxy-3,4-O-isopropylidene-L-glycero-L-talo-heptono-1,5-lactone 在 三氟乙酸 作用下， 反应 16.0h， 以100%的产率得到7-deoxy-L-glycero-L-talo-heptono-1,4-lactone
  参考文献：
  名称：

  Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose

  摘要：

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.

  DOI：

  10.1016/s0957-4166(00)80399-7
• 作为产物：
  描述：

  L-rhamnopyranose 在 硫酸 、 copper(II) sulfate 、 溶剂黄146 作用下， 反应 50.0h， 生成 7-deoxy-3,4-O-isopropylidene-L-glycero-L-talo-heptono-1,5-lactone
  参考文献：
  名称：

  Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose

  摘要：

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.

  DOI：

  10.1016/s0957-4166(00)80399-7

文献信息

• Mimics ofl-rhamnose: Synthesis of C-glycosides of L-rhamnofuranose and an α-azidoester as divergent intermediates for combinatorial generation of rhamnofuranose libraries
  作者：Juan C. Estevez、John Saunders、Gurdyal S. Besra、Patrick J. Brennan、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/0957-4166(96)00012-2

  日期：1996.2

  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.
• Ketals of L-rhamnoheptonolactones: Potential mimics of L-rhamnose
  作者：Joseph R. Wheatley、Annabel R. Beacham、Paul M. de Q. Lilley、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0957-4166(00)80399-7

  日期：1994.12

  Isopropylidene and cyclohexylidene ketals of gamma- and delta-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-1-glycero-1-galacto-hepta 1,5-lactone provides an example of a delta-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910.