6-O-acetyl-3-O-carbamoyl-4-O-methyl-D-glucal | 1234627-13-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-O-acetyl-3-O-carbamoyl-4-O-methyl-D-glucal
• CAS: 1234627-13-4
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: VSSXGIQOHCVFDR-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.08
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-3-O-carbamoyl-4-O-methyl-D-glucal 、 叔丁醇 在 dirhodium tetraacetate 、 二(叔丁基羰基氧基)碘苯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以71%的产率得到[(3aS,4R,6R,7S,7aR)-7-methoxy-4-[(2-methylpropan-2-yl)oxy]-2-oxo-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate
  参考文献：
  名称：

  New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group

  摘要：

  Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-D-mannosamine (ManNAc) and the corresponding sialic acids from D-glucal were established. Lipase-catalyzed regioselective transformation of n-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tertbutyl alcohol proceeded in manna-configured at C-2 as well as alpha- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.045
• 作为产物：
  描述：

  在 aluminum oxide 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以226 mg的产率得到6-O-acetyl-3-O-carbamoyl-4-O-methyl-D-glucal
  参考文献：
  名称：

  New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group

  摘要：

  Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-D-mannosamine (ManNAc) and the corresponding sialic acids from D-glucal were established. Lipase-catalyzed regioselective transformation of n-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tertbutyl alcohol proceeded in manna-configured at C-2 as well as alpha- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.045