2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 1347739-78-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• CAS: 1347739-78-9
• 化学式: C₅₆H₄₆Cl₃NO₁₆
• 分子量: 1095.34
• InChiKey: GNISEPMQYKVPFW-RQWIZDSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  76.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  218.57
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranoside 、 2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Facile syntheses of the disaccharide repeating unit of the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b and its dimer and trimer

  摘要：

  A highly efficient strategy for the preparation of a disaccharide-repeating unit of the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b, and its dimer and trimer, has been developed through a regio- and stereoselective manner using p-methoxylphenyl 2,4,6-tri-O-benzoyl-alpha-D-glucopyranoside and 3-O-allyloxycarbonyl-2,4-di-O-benzoy1-6-deoxy-alpha-L-talopyranosyl trichloroacetimidate as the key synthons. The target molecules were equipped with a p-methoxylphenyl handle at the reducing terminus to allow for their further functionalization and attachment to a carrier protein. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.001
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-glucopyranoside 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.33h， 生成 2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Facile syntheses of the disaccharide repeating unit of the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b and its dimer and trimer

  摘要：

  A highly efficient strategy for the preparation of a disaccharide-repeating unit of the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b, and its dimer and trimer, has been developed through a regio- and stereoselective manner using p-methoxylphenyl 2,4,6-tri-O-benzoyl-alpha-D-glucopyranoside and 3-O-allyloxycarbonyl-2,4-di-O-benzoy1-6-deoxy-alpha-L-talopyranosyl trichloroacetimidate as the key synthons. The target molecules were equipped with a p-methoxylphenyl handle at the reducing terminus to allow for their further functionalization and attachment to a carrier protein. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.001