1-methyl-2,3,4,6-tetra-O-(2-propynyl)-α-D-glucopyranoside | 13035-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-2,3,4,6-tetra-O-(2-propynyl)-α-D-glucopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-allyl-α-D-glucopyranoside；methyl-2,3,4,6-tetra-O-allyl-α-D-glucopyranoside；methyl-(tetra-O-allyl-α-D-glucopyranoside)；Methyl-(tetra-O-allyl-α-D-glucopyranosid)；(2R,3R,4S,5R,6S)-3,4,5-tris-allyloxy-2-allyloxymethyl-6-methoxy-tetrahydro-pyran；Methyl-2,3,4,6-tetra-O-allyl-α-D-glucopyranosid；(2S,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxane
• CAS: 13035-25-1
• 化学式: C₁₉H₃₀O₆
• 分子量: 354.444
• InChiKey: BQYMBCRFFFNQFU-FQBWVUSXSA-N

物化性质

• 沸点：
  182 °C(Press: 1.5 Torr)
• 密度：
  1.1519 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  1-methyl-2,3,4,6-tetra-O-(2-propynyl)-α-D-glucopyranoside 在 四(三苯基膦)钯 1,3-二甲基巴比妥酸 作用下， 以 甲醇 为溶剂， 以94%的产率得到alpha-甲基葡萄糖甙
  参考文献：
  名称：

  使用巴比妥酸衍生物对 Pd(0)-催化的烯丙基醚脱保护的显着溶剂效应：在选择性和连续去除烯丙基、甲基烯丙基和异戊二烯醚中的应用

  摘要：

  使用巴比妥酸衍生物在质子极性溶剂（如 MeOH 和 1,4-二恶烷水溶液中）中 Pd(0) 催化的烯丙基醚脱保护在室温下进行，而不会影响多种官能团。反应温度的控制允许烯丙基、甲代烯丙基和异戊二烯醚的选择性和连续裂解。配体对脱保护作用的研究表明，甲醇中反应性的提高是由于加速氧化加成到 Pd(0)。

  DOI：

  10.1055/s-2007-992352
• 作为产物：
  描述：

  3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以74%的产率得到1-methyl-2,3,4,6-tetra-O-(2-propynyl)-α-D-glucopyranoside
  参考文献：
  名称：

  WO2008/42688

  摘要：

  公开号：

文献信息

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  DOI：10.1080/00397911.2015.1005630

  日期：2015.6.18

  ABSTRACT Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction

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  DOI：10.1016/j.carres.2005.03.007

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