ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-2-methyl-D-glycero-D-talo-octonate | 109150-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-2-methyl-D-glycero-D-talo-octonate
• 英文别名: ethyl (3aR,4R,6S,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,6-trimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
• CAS: 109150-90-5
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: QIECKKRAQDPQFM-OQJJDWEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-2-methyl-D-glycero-D-talo-octonate 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (2S,4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-methyl-tetrahydro-pyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of C-(β-d-glycosyl) analogues of 3-deoxy-d-manno-2-octulosonic acid (Kdo) as potential inhibitors of CMP-Kdo synthetase

  摘要：

  Eight C-(beta-D-glycosyl) analogues (14-21) of Kdo (3-deoxy-D-manno-2-octulosonic acid) were obtained from isopropylidene-protected ester precursors and tested in vitro for their inhibitory activity on CMP-Kdo synthetase. None had more than minor inhibitory activity.

  DOI：

  10.1016/0008-6215(90)80066-c
• 作为产物：
  描述：

  ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-talo-octanoate 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 ethyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-2-methyl-D-glycero-D-talo-octonate
  参考文献：
  名称：

  Synthesis of C-glycosides of 3-deoxy-D-manno-2-octulosonic acid (KDO). Stereoselectivity in an enolate reaction

  摘要：

  DOI：

  10.1021/jo00226a010

文献信息

• LUTHMAN, KRISTINA;ORBE, MARTIN;WAGLUND, TOMMY;CLAESSON, ALF, J. ORG. CHEM., 52,(1987) N 17, 3777-3784
  作者：LUTHMAN, KRISTINA、ORBE, MARTIN、WAGLUND, TOMMY、CLAESSON, ALF

  DOI：——

  日期：——
• Synthesis of C-glycosides of 3-deoxy-D-manno-2-octulosonic acid (KDO). Stereoselectivity in an enolate reaction
  作者：Kristina Luthman、Martin Orbe、Tommy Waglund、Alf Claesson

  DOI：10.1021/jo00226a010

  日期：1987.8
• Synthesis of C-(β-d-glycosyl) analogues of 3-deoxy-d-manno-2-octulosonic acid (Kdo) as potential inhibitors of CMP-Kdo synthetase
  作者：Tommy W»glund、Kristina Luthman、Martin Orbe、Alf Claesson

  DOI：10.1016/0008-6215(90)80066-c

  日期：1990.10

  Eight C-(beta-D-glycosyl) analogues (14-21) of Kdo (3-deoxy-D-manno-2-octulosonic acid) were obtained from isopropylidene-protected ester precursors and tested in vitro for their inhibitory activity on CMP-Kdo synthetase. None had more than minor inhibitory activity.