methyl 2-acetamido-4-azido-3-O-benzoyl-2,4,6-trideoxy-α-D-galactopyranoside | 716329-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-4-azido-3-O-benzoyl-2,4,6-trideoxy-α-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-3-acetamido-5-azido-2-methoxy-6-methyloxan-4-yl] benzoate
• CAS: 716329-02-1
• 化学式: C₁₆H₂₀N₄O₅
• 分子量: 348.359
• InChiKey: JQYZUHURQBHMQD-NNPRGIHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-4-azido-3-O-benzoyl-2,4,6-trideoxy-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 sodium 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 16.08h， 生成 methyl 2-acetamido-4-amino-2,4,6-trideoxy-α-D-galactopyranoside
  参考文献：
  名称：

  An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

  摘要：

  Methyl 2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactopyranoside (10) was synthesized from D-glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O-3 of methyl 2-acetamido-2,6-dideoxy-alpha-D-glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di- and mono-benzyloxycarbonyl derivatives of 10 were also prepared.

  DOI：

  10.1081/car-120030468
• 作为产物：
  描述：

  methyl N-acetyl-D-glucosamine 在 palladium on activated charcoal 吡啶 、 四溴化碳 、 叠氮磷酸二苯酯 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -35.0~35.0 ℃ 、101.33 kPa 条件下， 反应 82.0h， 生成 methyl 2-acetamido-4-azido-3-O-benzoyl-2,4,6-trideoxy-α-D-galactopyranoside
  参考文献：
  名称：

  An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

  摘要：

  Methyl 2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactopyranoside (10) was synthesized from D-glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O-3 of methyl 2-acetamido-2,6-dideoxy-alpha-D-glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di- and mono-benzyloxycarbonyl derivatives of 10 were also prepared.

  DOI：

  10.1081/car-120030468

文献信息

• An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐<scp>D</scp>‐galactopyranose
  作者：Hong Liang、T. Bruce Grindley

  DOI：10.1081/car-120030468

  日期：2004.12.26

  Methyl 2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactopyranoside (10) was synthesized from D-glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O-3 of methyl 2-acetamido-2,6-dideoxy-alpha-D-glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di- and mono-benzyloxycarbonyl derivatives of 10 were also prepared.