benzyl-2,3-O-isopropylidene-4-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside | 1580516-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl-2,3-O-isopropylidene-4-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside
• CAS: 1580516-36-4
• 化学式: C₂₉H₄₂O₆Si
• 分子量: 514.734
• InChiKey: NDKVZZCROOHQCY-VKINHPFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl-2,3-O-isopropylidene-4-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， -20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 135.99h， 生成 1,4-dideoxy-1,4-{(R)-[(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]episulfoniumylidene}-D-arabinitol chloride
  参考文献：
  名称：

  Practical Synthesis of Neoponkoranol and its Related Sulfonium Salt, an Optimised Protocol using Isopropylidene as an Effective Protecting Group

  摘要：

  A practical synthesis of neoponkoranol and its related sulfonium salt as potent a-glucosidase inhibitors has been developed in which the key step of coupling reaction was optimised by using isopropylidene as an effective protecting group. The characteristic intramolecular cyclisation of the coupling precursor previously encountered as a side reaction has not been detected and coupling yields were dramatically improved in the present study.

  DOI：

  10.3184/174751913x13823645011477
• 作为产物：
  描述：

  benzyl 2,3-O-isopropylidene-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到benzyl-2,3-O-isopropylidene-4-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Practical Synthesis of Neoponkoranol and its Related Sulfonium Salt, an Optimised Protocol using Isopropylidene as an Effective Protecting Group

  摘要：

  A practical synthesis of neoponkoranol and its related sulfonium salt as potent a-glucosidase inhibitors has been developed in which the key step of coupling reaction was optimised by using isopropylidene as an effective protecting group. The characteristic intramolecular cyclisation of the coupling precursor previously encountered as a side reaction has not been detected and coupling yields were dramatically improved in the present study.

  DOI：

  10.3184/174751913x13823645011477