methyl (6R)-2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-6-C-ethynyl-6-O-tosyl-α-D-xylo-hexopyranoside | 1042438-87-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: methyl (6R)-2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-6-C-ethynyl-6-O-tosyl-α-D-xylo-hexopyranoside
• CAS: 1042438-87-8
• 化学式: C₄₆H₄₈O₉S
• 分子量: 776.948
• InChiKey: QEZGVCNJLKKRPN-CKYPCTIUSA-N

反应信息

• 作为反应物：
  描述：

  methyl (6R)-2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-6-C-ethynyl-6-O-tosyl-α-D-xylo-hexopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,3S,4R,5R,7S)-4-benzyloxy-5-[(S)-1,2-dibenzyloxyethyl]-7-ethynyl-3-methoxy-2,6-dioxabicyclo[3.2.1]octane
  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 (6R)-2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-6-C-ethynyl-α-D-xylo-hexopyranoside 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl (6R)-2,3-di-O-benzyl-4-deoxy-3-C-[(S)-1,2-dibenzyloxyethyl]-6-C-ethynyl-6-O-tosyl-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