4-methoxyphenyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside | 1192360-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS: 1192360-94-3
• 化学式: C₅₄H₅₈O₁₁
• 分子量: 883.048
• InChiKey: JNDKBHJEBMIFQZ-QVVQNYTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.85
• 重原子数：
  65.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 、 ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到4-methoxyphenyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Total synthesis of the heptasaccharide repeating unit of the iron-binding exopolysaccharide secreted by Klebsiella oxytoca BAS-10

  摘要：

  The first total synthesis of a heptasaccharide found in the iron-binding exopolysaccharide produced by Klebsiella oxytoca BAS-10 has been achieved in excellent yield using a block synthetic strategy. A trisaccharide glycosyl donor was stereoselectively coupled with a tetrasaccharide glycosyl acceptor using the trichloroacetimidate activation procedure. The yields and stereo outcome were excellent in each step of glycosylation. A late stage oxidation protocol was adopted for the oxidation of the primary hydroxyl group to the carboxylic functionality while keeping a secondary hydroxyl group unaffected. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.009
• 作为产物：
  描述：

  4-methoxyphenyl (3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 在 甲醇 、 palladium dichloride 作用下， 反应 6.0h， 以76%的产率得到4-methoxyphenyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Total synthesis of the heptasaccharide repeating unit of the iron-binding exopolysaccharide secreted by Klebsiella oxytoca BAS-10

  摘要：

  The first total synthesis of a heptasaccharide found in the iron-binding exopolysaccharide produced by Klebsiella oxytoca BAS-10 has been achieved in excellent yield using a block synthetic strategy. A trisaccharide glycosyl donor was stereoselectively coupled with a tetrasaccharide glycosyl acceptor using the trichloroacetimidate activation procedure. The yields and stereo outcome were excellent in each step of glycosylation. A late stage oxidation protocol was adopted for the oxidation of the primary hydroxyl group to the carboxylic functionality while keeping a secondary hydroxyl group unaffected. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.009