p-methoxyphenyl β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside | 1217343-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside
• 英文别名: p-methoxyphenyl β-D-glucopyranose-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside；Glc(b1-3)Rha(a1-3)Rha(a1-3)Rha(a)-O-Ph(4-OMe)；(2S,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-(4-methoxyphenoxy)-6-methyloxan-4-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1217343-82-2
• 化学式: C₃₁H₄₈O₁₉
• 分子量: 724.711
• InChiKey: NDJCOECGGKYVSC-OXOZBZCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  285
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 以330 mg的产率得到p-methoxyphenyl β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  从脂氮螺旋螺旋藻SR65合成与O-抗原有关的四糖。

  摘要：

  通过从商业上可获得的L-鼠李糖和D-葡萄糖开始的合适的保护基团操纵和立体选择性糖基化，已经完成了从脂杆螺旋藻SR65分离的LPS的四糖重复单元的精确合成。对-甲氧基苯基糖苷形式的目标寡糖适合通过OMP糖苷的选择性切割进一步形成糖缀合物。固氮螺菌属的植物生长促进细菌（PGPB）在植物的生长和发育中起着重要的作用。植物的根与微生物之间的相互作用受细胞表面碳水化合物聚合物（CPS，LPS等）支配。本基于合成的研究阐明了植物与微生物相互作用和未来生物肥料设计的各个方面。

  DOI：

  10.1016/j.carres.2009.11.024

文献信息

• Synthesis of Two Tetrasaccharides Related to the O-Antigen from<i>Azospirillum brasilense</i>S17 and<i>Azospirillum lipoferum</i>SR65
  作者：Hanqing Zhao、Huiqi Jia、Hongxia Duan、Jianjun Zhang、Daoquan Wang、Xiaomei Liang

  DOI：10.1080/07328301003786789

  日期：2010.4

  Synthesis of two isomeric tetrasaccharides, -D-Glup-(12)--L-Rhap-(13)--L- Rhap-(12)--L-Rhap (I) and -D-Glup-(13)--L-Rhap-(13)--L-Rhap-(13)--L-Rhap (II), the repeating units from the lipopolysaccharides of the nitrogen-fixing bacterium Azospirillum brasilense S17 and Azospirillum lipoferum SR65, was achieved via assembly of the building blocks 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate (2), p-methoxyphenyl 3,4-di-O-benzoyl--L-rhamnopyranoside (3), 3-O-allyloxycarbonyl-2,4-di-O-benzoyl--L-rhamnopyranosyl trichloroacetimidate (6), 2,3,4,6-tetra-O-benzoyl--D-glucopyranosyl trichloroacetimidate (8), and p-methoxy phenyl 2,4-di-O-benzoyl--L-rhamnopyranoside (14). Condensation of 3 with 6 or 8 provided the disaccharides 9 or 11, respectively. Deallyloxycarbonylation of 11 gave the disaccharide aceptor 12, while removal of the p-methoxyphenyl group in 9 followed by trichloroacetimidation of the anomeric hydroxyl group afforded the disaccharide donor 10. Meanwhile, disaccharide donor 16 and acceptor 18 were prepared from 6, 8, and 14 similarly. Finally, condensation of 10 with 12 or 16 with 18, followed by deprotection, gave the target tetrasaccharides I or II, respectively.
• Synthesis of a tetrasaccharide related to the O-antigen from Azospirillum lipoferum SR65
  作者：Prashant Ranjan Verma、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2009.11.024

  日期：2010.2

  lipoferum SR65 has been accomplished through suitable protecting group manipulations and stereoselective glycosylation starting from commercially available L-rhamnose and D-glucose. The target oligosaccharide in the form of its p-methoxyphenyl glycoside is suitable for further glycoconjugate formation via selective cleavage of the OMP glycoside. Plant growth-promoting bacteria (PGPB) of genus Azospirillum

  通过从商业上可获得的L-鼠李糖和D-葡萄糖开始的合适的保护基团操纵和立体选择性糖基化，已经完成了从脂杆螺旋藻SR65分离的LPS的四糖重复单元的精确合成。对-甲氧基苯基糖苷形式的目标寡糖适合通过OMP糖苷的选择性切割进一步形成糖缀合物。固氮螺菌属的植物生长促进细菌（PGPB）在植物的生长和发育中起着重要的作用。植物的根与微生物之间的相互作用受细胞表面碳水化合物聚合物（CPS，LPS等）支配。本基于合成的研究阐明了植物与微生物相互作用和未来生物肥料设计的各个方面。