phenyl 4,6-O-isopropylidene-β-D-glucopyranoside | 130720-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: phenyl 4,6-O-(1-methylethylidene)-beta-D-glucopyranoside；(4aR,6S,7R,8R,8aS)-2,2-dimethyl-6-phenoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 130720-64-8
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: XKYCHELBERAAIC-DHGKCCLASA-N

物化性质

• 沸点：
  464.2±45.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-isopropylidene-β-D-glucopyranoside 、 乙烯基正丁醚 在 palladium(II) trifluoroacetate 4,7-二苯基-1,10-菲罗啉 、 三乙胺 作用下， 反应 24.0h， 以36%的产率得到
  参考文献：
  名称：

  Optimized Synthesis of Vinyl Ether Sugars and Vinyl Glycosides through Transfer Vinylation Catalyzed by (4,7‐Ph₂‐phen)Pd(OOCCF₃)₂

  摘要：

  Sugar vinyl ethers and vinyl glycosides are conveniently synthesized by catalytic transfer vinylation with butyl vinyl ether, which serves as both the solvent and source of vinyl. The air-stable catalyst (4,7-diphenyl-1,10-phenanthroline)Pd(OOCCF(3))(2) is prepared in situ from commercially available components.

  DOI：

  10.1080/07328300802030852
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 苯基-BETA-葡萄糖吡喃糖苷 在 vanadyl triflate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以88%的产率得到phenyl 4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate

  摘要：

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.001

文献信息

• Optimized Synthesis of Vinyl Ether Sugars and Vinyl Glycosides through Transfer Vinylation Catalyzed by (4,7‐Ph₂‐phen)Pd(OOCCF₃)₂
  作者：Martin Bosch、Sean Handerson、Marcel Schlaf

  DOI：10.1080/07328300802030852

  日期：2008.5

  Sugar vinyl ethers and vinyl glycosides are conveniently synthesized by catalytic transfer vinylation with butyl vinyl ether, which serves as both the solvent and source of vinyl. The air-stable catalyst (4,7-diphenyl-1,10-phenanthroline)Pd(OOCCF(3))(2) is prepared in situ from commercially available components.
• O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
  作者：Chun-Cheng Lin、Mi-Dan Jan、Shiue-Shien Weng、Chang-Ching Lin、Chien-Tien Chen

  DOI：10.1016/j.carres.2006.04.001

  日期：2006.8

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.