n-propyl 2-acetamido-3-O-mesyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 217298-80-1

• 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: n-propyl 2-acetamido-3-O-mesyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-propoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] methanesulfonate
• CAS: 217298-80-1
• 化学式: C₁₉H₂₇NO₈S
• 分子量: 429.491
• InChiKey: FNQNPRSIXQBPEM-MGYGNFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  n-propyl 2-acetamido-3-O-mesyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 palladium dihydroxide 吡啶 、 盐酸 、 sodium azide 、 3 A molecular sieve 、 氢气 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇甲醚 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 104.0h， 生成 n-propyl 2-acetamido-3-amino-2,3-dideoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases:  A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor

  摘要：

  A short and effective synthesis of N-linked di- and trisaccharides is described. In a high-yielding reaction sequence, the glucosamine derivative 1 was transformed to the 3-azido-2,3-dideoxy sugar 2e under excellent stereocontrol. The LacNAc analogue 4d was synthesized as a single isomer in three steps starting from 2e. In a one-pot procedure, iminocyclitol 5 was transformed into aldehyde 6 and successfully used for reductive amination with 4c and 2f to give trisaccharide 8a and disaccharide 7a, respectively. This procedure represents a general strategy for the incorporation of an iminocyclitol as a transition-state mimic of the donor sugar moiety to the acceptor.

  DOI：

  10.1021/jo981245l
• 作为产物：
  描述：

  甲基磺酰氯 、 N-((2R,4aR,6R,7R,8R,8aS)-8-Hydroxy-2-phenyl-6-propoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 在 吡啶 作用下， 反应 24.0h， 以68%的产率得到n-propyl 2-acetamido-3-O-mesyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases:  A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor

  摘要：

  A short and effective synthesis of N-linked di- and trisaccharides is described. In a high-yielding reaction sequence, the glucosamine derivative 1 was transformed to the 3-azido-2,3-dideoxy sugar 2e under excellent stereocontrol. The LacNAc analogue 4d was synthesized as a single isomer in three steps starting from 2e. In a one-pot procedure, iminocyclitol 5 was transformed into aldehyde 6 and successfully used for reductive amination with 4c and 2f to give trisaccharide 8a and disaccharide 7a, respectively. This procedure represents a general strategy for the incorporation of an iminocyclitol as a transition-state mimic of the donor sugar moiety to the acceptor.

  DOI：

  10.1021/jo981245l

文献信息

• Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases:  A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor
  作者：Ralf Wischnat、Richard Martin、Chi-Huey Wong

  DOI：10.1021/jo981245l

  日期：1998.11.1

  A short and effective synthesis of N-linked di- and trisaccharides is described. In a high-yielding reaction sequence, the glucosamine derivative 1 was transformed to the 3-azido-2,3-dideoxy sugar 2e under excellent stereocontrol. The LacNAc analogue 4d was synthesized as a single isomer in three steps starting from 2e. In a one-pot procedure, iminocyclitol 5 was transformed into aldehyde 6 and successfully used for reductive amination with 4c and 2f to give trisaccharide 8a and disaccharide 7a, respectively. This procedure represents a general strategy for the incorporation of an iminocyclitol as a transition-state mimic of the donor sugar moiety to the acceptor.