1,2:5,6-di-O-isopropylidene-3-C-ethynyl-3-O-propargyl-α-D-allofuranose | 1242274-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-C-ethynyl-3-O-propargyl-α-D-allofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethynyl-2,2-dimethyl-6-prop-2-ynoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 1242274-09-4
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: MSWLEUANPXDTGA-GODIYZJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁炔二醇 、 1,2:5,6-di-O-isopropylidene-3-C-ethynyl-3-O-propargyl-α-D-allofuranose 在 Wilkinson's catalyst 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 以68%的产率得到1,2:5,6-di-O-isopropylidene-3-C,3-O-[o-{(3,4-bis(hydroxymethyl))}phenylenemethylene]-α-D-allofuranose
  参考文献：
  名称：

  The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

  摘要：

  The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.011
• 作为产物：
  描述：

  3-溴丙炔 、 3-C-ethynyl-1,2;5,6-di-O-isopropylidene-α-D-allo-hexofuranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到1,2:5,6-di-O-isopropylidene-3-C-ethynyl-3-O-propargyl-α-D-allofuranose
  参考文献：
  名称：

  The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides

  摘要：

  The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.011

文献信息

• The isochroman- and 1,3-dihydroisobenzofuran-annulation on carbohydrate templates via [2+2+2]-cyclotrimerization and synthesis of some tricyclic nucleosides
  作者：Sharad B. Suryawanshi、Mangesh P. Dushing、Rajesh G. Gonnade、C.V. Ramana

  DOI：10.1016/j.tet.2010.06.011

  日期：2010.8

  The synthesis of enantiopure tricyclic systems comprising isochroman or dihydroisobenzofuran units integrated with sugar templates has been documented. The alkyne cylotrimerization reaction has been employed with easily accessible sugar diynes for the key bicyclic ring construction and thus a provision to alter the functional groups on the newly formed aromatic rings. By selecting two representative trimerization products, we have synthesized the tricyclic nucleosides by simple synthetic manipulations. (c) 2010 Elsevier Ltd. All rights reserved.