1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose | 647832-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose
• CAS: 647832-29-9
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: MEMMNTSEAIMSCS-MIPOVIMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose 在 ruthenium trichloride 、 palladium on activated charcoal 吡啶 、 氢氧化钾 、 sodium periodate 、 三氟甲磺酸三甲基硅酯 、 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 氢气 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 [(2R,3R,4R,4aR,10bR)-3,4-diacetyloxy-8,9,10-trimethoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl acetate
  参考文献：
  名称：

  Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: remarkable 1,2-trans stereoselectivity

  摘要：

  The IDCP-promoted intramolecular C-glycosylation of pentenyl alpha-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an alpha-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3.Et2O. The IDCP-reaction product could be elaborated into a 2-(alpha-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.006
• 作为产物：
  描述：

  4-戊烯-1-醇 、 2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 四丁基溴化铵 作用下， 以 2,4,6-三甲基吡啶 为溶剂， 以71%的产率得到1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose
  参考文献：
  名称：

  Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: remarkable 1,2-trans stereoselectivity

  摘要：

  The IDCP-promoted intramolecular C-glycosylation of pentenyl alpha-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an alpha-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3.Et2O. The IDCP-reaction product could be elaborated into a 2-(alpha-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.006

文献信息

• Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-d-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation
  作者：Yuyong Ma、Gaoyan Lian、Yao Li、Biao Yu

  DOI：10.1039/c1cc11680k

  日期：——

  peracetyl glucopyranosyl ortho-hexynylbenzoate; experiments with substrates bearing deuterium labeled 2-O-acetyl or 4-O-acetyl groups indicated that the orthoacetate was derived from the 4-O-acetyl group, which provided a direct evidence for the remote participation of the 4-O-acyl group in glycosylation.

  在金（I）催化过乙酰基吡喃葡萄糖基邻己基苯甲酸酯的金（I）催化的糖苷化反应中观察到了3,6-二-O-乙酰基-1,2,4-O-邻乙酰基-α-D-吡喃葡萄糖的形成。用带有氘标记的2-O-乙酰基或4-O-乙酰基的底物进行的实验表明，原乙酸酯衍生自4-O-乙酰基，这为4-O-酰基的远程参与提供了直接证据在糖基化。