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 | 1347739-69-8

• 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: 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
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-[(2S,3R,4R,5R,6S)-3,5-dibenzoyloxy-6-methyl-4-prop-2-enoxycarbonyloxyoxan-2-yl]oxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 1347739-69-8
• 化学式: C₅₈H₅₂O₁₈
• 分子量: 1037.04
• InChiKey: NIZOYQUUBVLPJJ-PPBFJVQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  76
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  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 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以85%的产率得到p-methoxyphenyl 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：

  [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 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

文献信息

• 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.