(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1169497-69-1

• 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: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1169497-69-1
• 化学式: C₁₇H₂₅O₁₃P
• 分子量: 468.351
• InChiKey: YEAPRMPYKMXZIB-UHDSXZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 、 1,2,3-tri-O-benzyl-β-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 以77%的产率得到2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl-(1'->6)-(2'',3'',4'',6''-tetra-O-α-D-acetyl-mannopyranosyl-(1''->4))-1,2,3-tri-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  A unique approach to the synthesis of a dengue vaccine and the novel tetrasaccharide that results

  摘要：

  An approach to the development of a dengue vaccine by synthesizing the hexasaccharide epitope on the viral surface is examined. The stereochemical and structural challenges include the synthesis of a beta-mannoside bond. Synthesis of this bond is approached via a trisaccharide analogue portion of the epitope. A novel tetrasaccharide with a mannose-mannose anomeric linkage results in the Course of the synthetic attempts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.024
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 、 2-chloro-2-oxo-1,3,2-dioxaphosphorinane 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.08h， 以93%的产率得到(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  A unique approach to the synthesis of a dengue vaccine and the novel tetrasaccharide that results

  摘要：

  An approach to the development of a dengue vaccine by synthesizing the hexasaccharide epitope on the viral surface is examined. The stereochemical and structural challenges include the synthesis of a beta-mannoside bond. Synthesis of this bond is approached via a trisaccharide analogue portion of the epitope. A novel tetrasaccharide with a mannose-mannose anomeric linkage results in the Course of the synthetic attempts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.024