[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate | 1347739-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 1347739-65-4
• 化学式: C₂₂H₂₈O₁₀
• 分子量: 452.458
• InChiKey: MAGSUXKTAQBPOM-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 、 4-甲氧基苯酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate
  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