methyl 2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-α-D-xylo-hexopyranoside | 1042438-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-α-D-xylo-hexopyranoside
• CAS: 1042438-82-3
• 化学式: C₃₇H₄₂O₇
• 分子量: 598.736
• InChiKey: DHOBUOHRKAXPME-KWKSCYRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-α-D-xylo-hexopyranoside 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Synthetic Studies on the Carbohydrate Moiety of Amipurimycin

  摘要：

  The carbohydrate core of amipurimycin in its fully acetylated form was synthesized in 24 steps starting from commercially available methyl 4,6-O-benzylidene--D-glucopyranoside to give an overall yield of 1.5%. The late-stage intermediates involved were suitable for total synthesis of amipurimycin. It was further discovered that the branches and the protecting groups on the sugar rings of involved intermediates had a significant influence on their conformations, which in turn resulted in new and interesting cyclization reactions.

  DOI：

  10.1080/07328300802030787
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4-deoxy-3-C-[(R)-(ethoxycarbonyl)benzyloxymethyl]-6-O-trityl-α-D-xylo-hexopyranoside 、 溴甲苯 在 lithium aluminium tetrahydride 、 sodium hydride 、 甲酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙醚 为溶剂， 反应 3.0h， 以93%的产率得到methyl 2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthetic Studies on the Carbohydrate Moiety of Amipurimycin

  摘要：

  The carbohydrate core of amipurimycin in its fully acetylated form was synthesized in 24 steps starting from commercially available methyl 4,6-O-benzylidene--D-glucopyranoside to give an overall yield of 1.5%. The late-stage intermediates involved were suitable for total synthesis of amipurimycin. It was further discovered that the branches and the protecting groups on the sugar rings of involved intermediates had a significant influence on their conformations, which in turn resulted in new and interesting cyclization reactions.

  DOI：

  10.1080/07328300802030787