methyl 3-azido-4,6-O-benzylidene-2-(tert-butoxycarbonyl)amino-2,3-dideoxy-α-D-mannopyranoside | 353453-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-azido-4,6-O-benzylidene-2-(tert-butoxycarbonyl)amino-2,3-dideoxy-α-D-mannopyranoside
• CAS: 353453-24-4
• 化学式: C₁₉H₂₆N₄O₆
• 分子量: 406.439
• InChiKey: HLBWXNBMPIJYPU-DBHDPKECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  124.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-4,6-O-benzylidene-2-(tert-butoxycarbonyl)amino-2,3-dideoxy-α-D-mannopyranoside 在 platinum(IV) oxide 吡啶 、 盐酸 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 硝基甲烷 、 水 为溶剂， 反应 168.5h， 生成 2-acetamido-3-(tert-butoxycarbonyl)amino-2,3-dideoxy-D-mannopyranose
  参考文献：
  名称：

  Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-α,β-d-mannosamine as substrates for N-acetylneuraminic acid aldolase

  摘要：

  The synthesis of 3-azido-3-deoxy, 3-amino-3-deoxy and 3-N-tert-butyloxycarbonyl-3-deoxy derivatives of 2-acetamido-2-deoxy-alpha, beta -D-mannose (N-acetyl-alpha, beta -D-mannosamine, ManNAc), is presented. The 3-azido-3-deoxy- and 3-N-telt-butyloxycarbonyl compounds were further characterised as their peracetates. A preliminary study has found that these C-3 nitrogen-substituted derivatives of ManNAc not to be substrates for Neu5Ac aldolase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00091-x
• 作为产物：
  描述：

  2-azido-2-deoxy-4,6-O-(phenylmethylene)methyl-α-D-altropyranoside 在 platinum(IV) oxide 吡啶 、 sodium azide 、 氢气 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 58.0h， 生成 methyl 3-azido-4,6-O-benzylidene-2-(tert-butoxycarbonyl)amino-2,3-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-α,β-d-mannosamine as substrates for N-acetylneuraminic acid aldolase

  摘要：

  The synthesis of 3-azido-3-deoxy, 3-amino-3-deoxy and 3-N-tert-butyloxycarbonyl-3-deoxy derivatives of 2-acetamido-2-deoxy-alpha, beta -D-mannose (N-acetyl-alpha, beta -D-mannosamine, ManNAc), is presented. The 3-azido-3-deoxy- and 3-N-telt-butyloxycarbonyl compounds were further characterised as their peracetates. A preliminary study has found that these C-3 nitrogen-substituted derivatives of ManNAc not to be substrates for Neu5Ac aldolase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00091-x