ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside | 1215022-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS: 1215022-03-9
• 化学式: C₄₅H₄₇NO₁₁S
• 分子量: 809.934
• InChiKey: YFCBYFNXRWNXPG-OSLCOLGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  128.29
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside 、 2-(4-methoxyphenoxy)ethyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-3,4-di-O-benzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到2-(4-methoxyphenoxy)ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1->2)-[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)]-3,4-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide corresponding to the teichoic acid from the cell wall of Streptomyces sp. VKM Ac-2275

  摘要：

  A concise chemical synthesis of a tetrasaccharide found in the teichoic acid from the cell wall of Streptomyces sp. VKM Ac-2275 was achieved in high yield. A [2+2] block synthetic strategy has been adopted for the construction of the target tetrasaccharide by exploiting the orthogonal property of a thioglycoside. For the first time, the 2-(4-methoxyphenoxy) ethyl group has been used as the anomeric protecting group to make the glycone moiety with a readily available linker for its conjugation to a protein without destroying the cyclic structure at the reducing end. Yields were high in all of the intermediate steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.035
• 作为产物：
  描述：

  ETHYL4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-1-THIO-Β-D-GLUCOPYRANOSIDE乙基4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚氨基-1-硫代-Β-D-吡喃葡萄糖苷 、 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 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到ethyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide corresponding to the teichoic acid from the cell wall of Streptomyces sp. VKM Ac-2275

  摘要：

  A concise chemical synthesis of a tetrasaccharide found in the teichoic acid from the cell wall of Streptomyces sp. VKM Ac-2275 was achieved in high yield. A [2+2] block synthetic strategy has been adopted for the construction of the target tetrasaccharide by exploiting the orthogonal property of a thioglycoside. For the first time, the 2-(4-methoxyphenoxy) ethyl group has been used as the anomeric protecting group to make the glycone moiety with a readily available linker for its conjugation to a protein without destroying the cyclic structure at the reducing end. Yields were high in all of the intermediate steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.035