tert-butyl 2-acetamido-2-deoxy-α-D-mannopyranoside | 1234627-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• 英文别名: N-[(2R,3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2-methylpropan-2-yl)oxy]oxan-3-yl]acetamide
• CAS: 1234627-20-3
• 化学式: C₁₂H₂₃NO₆
• 分子量: 277.318
• InChiKey: PXQDIFJAITZUPX-RCZSTQMZSA-N

物化性质

• 沸点：
  517.6±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-acetamido-2-deoxy-α-D-mannopyranoside 在 水 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以67%的产率得到N-acetyl-D-mannosamine
  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：

  ((3aS,4R,6R,7S,7aR)-7-acetoxy-4-(tert-butoxy)-2-oxohexahydro-4H-pyrano[3,4-d]oxazol-6-yl)methyl acetate 、 乙酸酐 在 lithium hydroxide monohydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以100%的产率得到tert-butyl 2-acetamido-2-deoxy-α-D-mannopyranoside
  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

文献信息

• New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group
  作者：Jordi Calveras、Yasuhito Nagai、Israt Sultana、Yuji Ueda、Toshinori Higashi、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.tet.2010.04.045

  日期：2010.6

  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.