diethyl (4R,5S,6R)-3-acetamido-5,7-O-benzylidene-4,6-dihydroxy-1-heptene phosphonate | 677309-33-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl (4R,5S,6R)-3-acetamido-5,7-O-benzylidene-4,6-dihydroxy-1-heptene phosphonate
• CAS: 677309-33-0
• 化学式: C₂₀H₃₀NO₈P
• 分子量: 443.434
• InChiKey: PDECOWWLKCASFY-JATGDLEKSA-N

物化性质

• 沸点：
  694.0±55.0 °C(predicted)
• 密度：
  1.260±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123.55
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl (4R,5S,6R)-3-acetamido-5,7-O-benzylidene-4,6-dihydroxy-1-heptene phosphonate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 ((2R,4aR,6R,7S,8R,8aS)-7-Acetylamino-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Concise and stereocontrolled syntheses of phosphonate C-glycoside analogues of β-d-ManNAc and β-d-GlcNAc 1-O-phosphates

  摘要：

  Diethyl C-(2 -deoxy-2-acetamido- beta-D-mannopyranosyl)methylphosphonate and dimethyl C-(2-deoxy-2-acetamido-beta-D-glucopyranosyl)methylphosphonate were stereoselectively prepared from N-acetyl D-glucosamine. Routes to such compounds starting frorn D-GlcNAc have been problematic, but we have found short and efficient implementations of this highly desirable transformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.081
• 作为产物：
  描述：

  亚甲基二磷酸四乙酯 、 2-acetamido-4,6-O-benzylidene-2-deoxy-D-glucopyranose 在 正丁基锂 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到diethyl (4R,5S,6R)-3-acetamido-5,7-O-benzylidene-4,6-dihydroxy-1-heptene phosphonate
  参考文献：
  名称：

  Concise and stereocontrolled syntheses of phosphonate C-glycoside analogues of β-d-ManNAc and β-d-GlcNAc 1-O-phosphates

  摘要：

  Diethyl C-(2 -deoxy-2-acetamido- beta-D-mannopyranosyl)methylphosphonate and dimethyl C-(2-deoxy-2-acetamido-beta-D-glucopyranosyl)methylphosphonate were stereoselectively prepared from N-acetyl D-glucosamine. Routes to such compounds starting frorn D-GlcNAc have been problematic, but we have found short and efficient implementations of this highly desirable transformation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.081