n-propyl 2-acetamido-3-azido-6-O-benzyl-2,3-dideoxy-β-D-glucopyranoside | 217298-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: n-propyl 2-acetamido-3-azido-6-O-benzyl-2,3-dideoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-4-azido-5-hydroxy-6-(phenylmethoxymethyl)-2-propoxyoxan-3-yl]acetamide
• CAS: 217298-84-5
• 化学式: C₁₈H₂₆N₄O₅
• 分子量: 378.428
• InChiKey: JCBDDVWBCWKVOV-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  n-propyl 2-acetamido-3-azido-6-O-benzyl-2,3-dideoxy-β-D-glucopyranoside 在 sodium hydroxide 、 三氟化硼 、 sodium methylate 、 sodium cyanoborohydride 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 n-propyl 2-acetamido-2,3-dideoxy-4-O-(β-D-galactopyranosyl)-6-O-benzyl-3-amino-3-N-{2-[N-(1,3,4,5-tetra-O-benzyl-β-L-homofuconojirimycinyl)]ethyl}-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：

  n-propyl 2-acetamido-3-O-mesyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 吡啶 、 盐酸 、 sodium azide 、 3 A molecular sieve 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 n-propyl 2-acetamido-3-azido-6-O-benzyl-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

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.