3-O-allyloxycarbonyl-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl trichloroacetimidate | 1235993-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl trichloroacetimidate
• 英文别名: [(2S,3R,4R,5R,6S)-5-benzoyloxy-2-methyl-4-prop-2-enoxycarbonyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 1235993-61-9
• 化学式: C₂₆H₂₄Cl₃NO₉
• 分子量: 600.837
• InChiKey: COFMKERDOKXGKW-DBGRRDFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-allyloxycarbonyl-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl trichloroacetimidate 、 p-methoxyphenyl 2,4,6-tri-O-benzoyl-α-D-glucopyranoside 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82%的产率得到p-methoxyphenyl 3-allyloxycarbonyl-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：

  3-O-allyloxycarbonyl-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以2.6 g的产率得到3-O-allyloxycarbonyl-2,4-di-O-benzoyl-6-deoxy-α-L-talopyranosyl trichloroacetimidate
  参考文献：
  名称：

  有效合成6-脱氧塔洛糖四糖，其与c型血清放线杆菌聚合产生的抗原性O-多糖有关。

  摘要：

  精确合成6-脱氧-α-L-塔洛糖四糖，6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp-（1-> 2） -6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp，是来自血清型c的放线杆菌的OPS的二糖重复单元的二聚体，已经通过合适的方法完成。从可商购的L-鼠李糖开始的保护基操纵和立体选择性糖基化。对-甲氧基苯基糖苷形式的目标寡糖适合通过该基团的选择性切割进一步形成糖缀合物。

  DOI：

  10.1016/j.carres.2010.04.009

文献信息

• Efficient synthesis of a 6-deoxytalose tetrasaccharide related to the antigenic O-polysaccharide produced by Aggregatibacter actinomycetemcomitans serotype c
  作者：Xiangyan Cai、Guanghui Zong、Yanjun Xu、Jianjun Zhang、Xiaomei Liang、Daoquan Wang

  DOI：10.1016/j.carres.2010.04.009

  日期：2010.6

  actinomycetemcomitans serotype c, has been accomplished through suitable protecting group manipulations and stereoselective glycosylation starting from commercially available L-rhamnose. The target oligosaccharide in the form of its p-methoxyphenyl glycoside is suitable for further glycoconjugate formation via selective cleavage of this group.

  精确合成6-脱氧-α-L-塔洛糖四糖，6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp-（1-> 2） -6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp，是来自血清型c的放线杆菌的OPS的二糖重复单元的二聚体，已经通过合适的方法完成。从可商购的L-鼠李糖开始的保护基操纵和立体选择性糖基化。对-甲氧基苯基糖苷形式的目标寡糖适合通过该基团的选择性切割进一步形成糖缀合物。
• Facile syntheses of the disaccharide repeating unit of the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b and its dimer and trimer
  作者：Guanghui Zong、Xiangyan Cai、Xiaomei Liang、Jianjun Zhang、Daoquan Wang

  DOI：10.1016/j.carres.2011.09.001

  日期：2011.11

  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.