(3aS,4R,6R,7S,7aR)-4-(tert-butoxy)-7-hydroxy-6-(hydroxymethyl)tetrahydro-4H-pyrano[3,4-d]oxazol-2(3H)-one | 1234627-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6R,7S,7aR)-4-(tert-butoxy)-7-hydroxy-6-(hydroxymethyl)tetrahydro-4H-pyrano[3,4-d]oxazol-2(3H)-one
• CAS: 1234627-18-9
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: QPYHVBTXSGHWKO-ANZWQOBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  97.25
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 (3aS,4R,6R,7S,7aR)-4-(tert-butoxy)-7-hydroxy-6-(hydroxymethyl)tetrahydro-4H-pyrano[3,4-d]oxazol-2(3H)-one 在 solid phase supported Burkholderia cepacia lipase 作用下， 反应 3.0h， 以99%的产率得到((3aS,4R,6R,7S,7aR)-4-(tert-butoxy)-7-hydroxy-2-oxohexahydro-4H-pyrano[3,4-d]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：

  ((3aS,4R,6R,7S,7aR)-7-acetoxy-4-(tert-butoxy)-2-oxohexahydro-4H-pyrano[3,4-d]oxazol-6-yl)methyl acetate 在 lithium hydroxide monohydrate 、 乙醇 作用下， 反应 3.0h， 以97%的产率得到(3aS,4R,6R,7S,7aR)-4-(tert-butoxy)-7-hydroxy-6-(hydroxymethyl)tetrahydro-4H-pyrano[3,4-d]oxazol-2(3H)-one
  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