methyl 2,6-dideoxy-4-O-(p-methoxybenzyl)-2-(p-tolylthio)-α-L-idopyranosyl-(1->6)-2,3-O-isopropylidene-α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-4-O-(p-methoxybenzyl)-2-(p-tolylthio)-α-L-idopyranosyl-(1->6)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: (2S,3R,4S,5S,6S)-2-[[(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-5-[(4-methoxyphenyl)methoxy]-6-methyl-3-(4-methylphenyl)sulfanyloxan-4-ol
• 化学式: C₃₁H₄₂O₉S
• 分子量: 590.735
• InChiKey: AUMALXSYRNVVOM-HXUMVSNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  p-tolyl 2,3-anhydro-6-deoxy-4-O-(p-methoxybenzyl)-1-thio-β-L-gulopyranoside 、 甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到methyl 2,6-dideoxy-4-O-(p-methoxybenzyl)-2-(p-tolylthio)-α-L-idopyranosyl-(1->6)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

  摘要：

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.

  DOI：

  10.1021/jo900131a

文献信息

• 2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1021/jo900131a

  日期：2009.3.20

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.