methyl 2-azido-3,4-di-O-benzyl-2-deoxy-α-D-manno-hexodialdo-1,5-pyranoside | 352654-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-3,4-di-O-benzyl-2-deoxy-α-D-manno-hexodialdo-1,5-pyranoside
• 英文别名: (2S,3S,4R,5S,6S)-5-azido-6-methoxy-3,4-bis(phenylmethoxy)oxane-2-carbaldehyde
• CAS: 352654-93-4
• 化学式: C₂₁H₂₃N₃O₅
• 分子量: 397.431
• InChiKey: DVXCIXINAGQVSX-XNTOXWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3,4-di-O-benzyl-2-deoxy-α-D-manno-hexodialdo-1,5-pyranoside 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 13.5h， 生成 methyl 6-O-acetyl-7-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride

  摘要：

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00078-7
• 作为产物：
  描述：

  methyl 2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.28h， 以96%的产率得到methyl 2-azido-3,4-di-O-benzyl-2-deoxy-α-D-manno-hexodialdo-1,5-pyranoside
  参考文献：
  名称：

  Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride

  摘要：

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00078-7

文献信息

• Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-d-hexopyranosides with allyloxymethylmagnesium chloride
  作者：Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/s0008-6215(01)00078-7

  日期：2001.5

  Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta -D-gluco and alpha -D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta -D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by H-1 NMR data. (C) 2001 Elsevier Science Ltd. All rights reserved.