3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose | 1236307-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose
• 英文别名: [(2R)-2-[(3aR,5S,6S,6aR)-6-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methylsulfonyloxyethyl] methanesulfonate
• CAS: 1236307-87-1
• 化学式: C₂₇H₃₈O₁₀S₂Si
• 分子量: 614.81
• InChiKey: QPJUGKWNIYWOKS-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以9.1 g的产率得到3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-xylo-5-hexenofuranose
  参考文献：
  名称：

  Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols

  摘要：

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.074
• 作为产物：
  描述：

  甲基磺酰氯 、 3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 作用下， 以95%的产率得到3-O-[(tert-butyl)-diphenylsilyl]-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose
  参考文献：
  名称：

  Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols

  摘要：

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.074

文献信息

• Formal synthesis of (+)-varitriol. Application of Pd(II)/Cu(II)-catalysed bicyclisation of unsaturated polyols
  作者：Miroslav Palík、Oľga Karlubíková、Daniela Lackovičová、Angelika Lásiková、Tibor Gracza

  DOI：10.1016/j.tet.2010.04.074

  日期：2010.7

  A formal and improved synthesis of natural (+)-varitriol from D-glucose and dimethyl L-tartrate, respectively, are reported. The key steps are the Pd(II)/Cu(II)-catalysed bicyclisation of O-benzyl protected triols L-xylo-15 and L-xylo-15/L-lyxo-15, respectively, followed by ring opening of intermediate dianhydro-L-gulitol 16. The syntheses of key intermediate of the furanoside portion 17 proceed in 13 steps with 5% (from bisacetone-D-glucose), and in 12 steps with 7.6% over-all yield from dimethyl L-tartrate, respectively. (C) 2010 Elsevier Ltd. All rights reserved.