methyl 4-O-benzyl-2,3-O-naphthylidene-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 1028832-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzyl-2,3-O-naphthylidene-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: (2R,3aR,4R,6S,7S,7aR)-4-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-methyl-2-naphthalen-2-yl-7-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 1028832-84-9
• 化学式: C₅₂H₅₄O₁₀
• 分子量: 838.995
• InChiKey: XHOJQYRVHKUFET-PSDADPFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  62
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzyl-2,3-O-naphthylidene-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到methyl 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
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside methyl 4'-O-benzyl-3'-O-trimethylsilyl-1'-thio-α-L-rhamnopyranoside 4-2'-2-naphthylidene acetal 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以68%的产率得到methyl 4-O-benzyl-2,3-O-naphthylidene-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

文献信息

• Stereoselective Synthesis of β-<scp>l</scp>-Rhamnopyranosides
  作者：Yong Joo Lee、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/ja801574q

  日期：2008.5.1

  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.