4-methoxyphenyl (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 | 1203549-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (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: 1203549-94-3
• 化学式: C₉₄H₁₀₀O₂₁
• 分子量: 1565.82
• InChiKey: BCNZSVATOOHDGK-GVYKDDNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.93
• 重原子数：
  115.0
• 可旋转键数：
  36.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  215.83
• 氢给体数：
  2.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-4-O-benzyl-3-O-(p-methoxybenzyl)-1-thio-α-L-rhamnopyranoside 、 4-methoxyphenyl (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83%的产率得到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
  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-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以98%的产率得到4-methoxyphenyl (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