methyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 1028832-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS: 1028832-94-1
• 化学式: C₇₂H₇₈O₁₄
• 分子量: 1167.4
• InChiKey: QTLISFBTUCZUDU-ZIINYCLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.86
• 重原子数：
  86.0
• 可旋转键数：
  27.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140.22
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以96%的产率得到methyl α-L-rhamnopyranosyl-(1->3)-β-L-rhamnopyranosyl-(1->4)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-l-Rhamnopyranosides

  摘要：

  Stereoselective construction of 1,2-cis-beta-L-rhamnopyranoside was achieved by our effective methodology using naphthylmethyl (NAP) ether-mediated intramolecular aglycon delivery (IAD). The complete stereoselective synthesis of the bacterial extracellular polysaccharide, alpha-L-Rhap-(1 -> 3)-beta-L-Rhap-(1 -> 4)Glcp from Sphaerotilus natans, was successfully accomplished, clearly demonstrating that the NAP-IAD methodology is highly versatile.

  DOI：

  10.1021/ja801574q
• 作为产物：
  描述：

  methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到methyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-l-Rhamnopyranosides

  摘要：

  Stereoselective construction of 1,2-cis-beta-L-rhamnopyranoside was achieved by our effective methodology using naphthylmethyl (NAP) ether-mediated intramolecular aglycon delivery (IAD). The complete stereoselective synthesis of the bacterial extracellular polysaccharide, alpha-L-Rhap-(1 -> 3)-beta-L-Rhap-(1 -> 4)Glcp from Sphaerotilus natans, was successfully accomplished, clearly demonstrating that the NAP-IAD methodology is highly versatile.

  DOI：

  10.1021/ja801574q