methyl 4-O-benzyl-2-O-(2-naphthylmethyl)-3-O-trimethylsilyl-1-thio-α-L-rhamnopyranoside | 1028832-75-8

• 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-O-(2-naphthylmethyl)-3-O-trimethylsilyl-1-thio-α-L-rhamnopyranoside
• 英文别名: trimethyl-[(2S,3S,4R,5R,6S)-2-methyl-6-methylsulfanyl-5-(naphthalen-2-ylmethoxy)-3-phenylmethoxyoxan-4-yl]oxysilane
• CAS: 1028832-75-8
• 化学式: C₂₈H₃₆O₄SSi
• 分子量: 496.743
• InChiKey: DIPCFSVZCPXKDQ-OWNPQWGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 methyl 4-O-benzyl-2-O-(2-naphthylmethyl)-3-O-trimethylsilyl-1-thio-α-L-rhamnopyranoside 在 4 A molecular sieve 、 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 4.0h， 以93%的产率得到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
  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：

  三甲基氯硅烷 、 methyl 4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-L-rhamnopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以93%的产率得到methyl 4-O-benzyl-2-O-(2-naphthylmethyl)-3-O-trimethylsilyl-1-thio-α-L-rhamnopyranoside
  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.