3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate | 1260731-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate
• CAS: 1260731-17-6
• 化学式: C₅₁H₄₄Cl₃NO₉S
• 分子量: 953.337
• InChiKey: WEAMQAFSPXHQNW-UCDSGCLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.77
• 重原子数：
  65.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122.6
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.84h， 以76%的产率得到methyl 3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoelectronic Effects Determine Oxacarbenium vs β-Sulfonium Ion Mediated Glycosylations

  摘要：

  Activation of a glycosyl donor protected with a 2-O-(S)-(phenylthiomethyl)benzyl ether chiral auxiliary results in the formation of an anomeric beta-sulfonium ion, which can be displaced with sugar alcohols to give corresponding a-glycosides. Sufficient deactivation of such glycosyl donors by electron-withdrawing protecting groups is, however, critical to avoid glycosylation of an oxacarbenium ion intermediate. The latter type of glycosylation pathway can also be suppressed by installing additional substituents in the chiral auxiliary.

  DOI：

  10.1021/ol1027267
• 作为产物：
  描述：

  t-butyldimethylsilyl 3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-β-D-glucopyranoside 在 sodium hydride 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 0.17h， 生成 3-O-benzoyl-4-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-{(1S)-phenyl-2-phenylsulfanyl-ethyl}-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Stereoelectronic Effects Determine Oxacarbenium vs β-Sulfonium Ion Mediated Glycosylations

  摘要：

  Activation of a glycosyl donor protected with a 2-O-(S)-(phenylthiomethyl)benzyl ether chiral auxiliary results in the formation of an anomeric beta-sulfonium ion, which can be displaced with sugar alcohols to give corresponding a-glycosides. Sufficient deactivation of such glycosyl donors by electron-withdrawing protecting groups is, however, critical to avoid glycosylation of an oxacarbenium ion intermediate. The latter type of glycosylation pathway can also be suppressed by installing additional substituents in the chiral auxiliary.

  DOI：

  10.1021/ol1027267