4-methoxyphenyl [2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1203549-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl [2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 1203549-96-5
• 化学式: C₁₀₉H₁₁₈O₂₆
• 分子量: 1844.12
• InChiKey: JXIRPMQEEUAXRJ-VEYWENLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.58
• 重原子数：
  135.0
• 可旋转键数：
  42.0
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  269.82
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-5-ethylsulfanyl-3,4-bis(phenylmethoxy)oxolane 、 4-methoxyphenyl [2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 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78%的产率得到4-methoxyphenyl (2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl)-(1->3)-[2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise Synthesis of a Hexasaccharide Related to the Adhesin Receptor of Streptococcus oralis ATCC 55229

  摘要：

  A concise synthesis of a hexasaccharide related to the adhesin receptor of Streptococcus oralis ATCC 55229 (previously characterized as Streptococcus sanguis H1) has been achieved in excellent yield. A general glycosylation condition has been used throughout the synthetic scheme. All glycosylation steps and protecting group functionalization steps are high yielding and suitable for scale-up preparation.

  DOI：

  10.1080/07328300903261554
• 作为产物：
  描述：

  4-methoxyphenyl [2-O-acetyl-4-O-benzyl-3-O-(4-methoxybenzyl)-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到4-methoxyphenyl [2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl]-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise Synthesis of a Hexasaccharide Related to the Adhesin Receptor of Streptococcus oralis ATCC 55229

  摘要：

  A concise synthesis of a hexasaccharide related to the adhesin receptor of Streptococcus oralis ATCC 55229 (previously characterized as Streptococcus sanguis H1) has been achieved in excellent yield. A general glycosylation condition has been used throughout the synthetic scheme. All glycosylation steps and protecting group functionalization steps are high yielding and suitable for scale-up preparation.

  DOI：

  10.1080/07328300903261554