methyl 3-O-allyl-β-D-glucopyranoside | 322479-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-allyl-β-D-glucopyranoside
• CAS: 322479-17-4
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: JUQGZDQHBMDAKB-GRDBIXFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-β-D-glucopyranoside 在 乙酸酐 、 对甲苯磺酸 、 二甲基亚砜 作用下， 反应 16.33h， 生成 (4aR,6R,8S,8aR)-8-Allyloxy-6-methoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one
  参考文献：
  名称：

  New Factors Governing Stereoselectivity in Borohydride Reductions ofβ-D-Glycoside-2-uloses − The Peculiar Effect of “Activated” DMSO

  摘要：

  Comparative evaluation of the manno/gluco ratios obtained in the conventional reductions of beta -D-glucoside-2-uloses (1-4, 13 and 14) reveals the influence of the substitution pattern: the presence of a 4,6-O-acetal function results in lower stereoselectivity in the monosaccharide-uloside cases and low stereoselectivity in the disaccharide-uloside cases, while the absence of a 4,6-O-acetal group provides distinctly higher stereoselectivity. The 3-O-benzyl and 3-O-allyl ethers vicinal to the carbonyl to be reduced have a similar influence on the steric outcome of the carbonyl reduction. A peculiar effect of acetoxydimethylsulfonium acetate ("activated" DMSO) was observed. In all cases, its presence strongly increased the manno-selectivity of the reduction. A simple, preparatively expedient, commonly suitable protocol has been elaborated for achieving high manno-selectivities and, hence, satisfactory yields.

  DOI：

  10.1002/1099-0690(200012)2000:23<3931::aid-ejoc3931>3.0.co;2-w
• 作为产物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 methyl 3-O-allyl-β-D-glucopyranoside
  参考文献：
  名称：

  Corrie, John E. T., Journal of the Chemical Society. Perkin transactions I, 1993, # 18, p. 2161 - 2166

  摘要：

  DOI：