allyl O-(2,3-di-O-acetyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 152733-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl O-(2,3-di-O-acetyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 152733-61-4
• 化学式: C₂₈H₄₀O₁₆
• 分子量: 632.616
• InChiKey: JESAKGWTYRNRGX-DVCSACCXSA-N

物化性质

• 沸点：
  652.0±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  186.88
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  allyl O-(2,3-di-O-acetyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 16.0h， 以90%的产率得到Allyl 2,3,6,2',3'-Penta-O-acetyl-β-maltoside
  参考文献：
  名称：

  Preparation of 4,6-cyclo-4,6-dideoxy-hexopyranoses by palladium-mediated intramolecular cyclodehalogenation

  摘要：

  4,6-Cyclo-4,6-dideoxy-hexopyranoses were obtained by palladium-mediated intramolecular cyclodehalogenation. Thus, methyl 2,3-di-O-acetyl-4,6-dideoXY-4,6-diiodo-beta-D-galactopyranoside (3) afforded methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-beta-D-galactopyranoside (5) in 56% yield upon treatment with hydrogen in the presence of palladium-on-charcoal and diethylamine. The structure of 5 was proven by MS, NMR including NOE measurements, and by independent conversion of 4 to 5 by zinc-mediated Wurtz synthesis. Similarly, methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranoside (6) and O-(2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranosyl)-(l --> 4)-1,2,3,6-tetra-0-acetyl-beta-D-glucopyranose (17) were obtained along with the respective 4,6-dideoxy analogues. Also methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-beta-D-glucopyranoside (19) gave galacto-configured 5 stereoselectively.

  DOI：

  10.1016/0008-6215(93)80074-o
• 作为产物：
  描述：

  乙酸酐 、 allyl O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 吡啶 作用下， 反应 16.0h， 以89%的产率得到allyl O-(2,3-di-O-acetyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation of 4,6-cyclo-4,6-dideoxy-hexopyranoses by palladium-mediated intramolecular cyclodehalogenation

  摘要：

  4,6-Cyclo-4,6-dideoxy-hexopyranoses were obtained by palladium-mediated intramolecular cyclodehalogenation. Thus, methyl 2,3-di-O-acetyl-4,6-dideoXY-4,6-diiodo-beta-D-galactopyranoside (3) afforded methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-beta-D-galactopyranoside (5) in 56% yield upon treatment with hydrogen in the presence of palladium-on-charcoal and diethylamine. The structure of 5 was proven by MS, NMR including NOE measurements, and by independent conversion of 4 to 5 by zinc-mediated Wurtz synthesis. Similarly, methyl 2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranoside (6) and O-(2,3-di-O-acetyl-4,6-cyclo-4,6-dideoxy-alpha-D-galactopyranosyl)-(l --> 4)-1,2,3,6-tetra-0-acetyl-beta-D-glucopyranose (17) were obtained along with the respective 4,6-dideoxy analogues. Also methyl 2,3-di-O-acetyl-4,6-dideoxy-4,6-diiodo-beta-D-glucopyranoside (19) gave galacto-configured 5 stereoselectively.

  DOI：

  10.1016/0008-6215(93)80074-o