p-methoxylphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside | 1124220-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxylphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: p-methoxyphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside；[(2S,3S,4S,5R,6S)-4-benzoyloxy-5-hydroxy-6-(4-methoxyphenoxy)-2-methyloxan-3-yl] benzoate
• CAS: 1124220-92-3
• 化学式: C₂₇H₂₆O₈
• 分子量: 478.499
• InChiKey: AWRZQLXSNSFYAS-PWPHSLCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-methoxylphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Two Tetrasaccharides Related to the O-Antigen fromAzospirillum brasilenseS17 andAzospirillum lipoferumSR65

  摘要：

  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.

  DOI：

  10.1080/07328301003786789
• 作为产物：
  描述：

  苯甲酰氯 、 4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以69%的产率得到p-methoxylphenyl 3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  从水生细菌气单胞菌207分离的O特异性多糖的重复单元的合成

  摘要：

  Bestiarum 207气单胞菌是对水产养殖有严重影响的细菌病原体。在最近的研究中，来自气单胞菌的OPS抗原的结构被鉴定为五糖重复单元。报道了五糖重复单元及其衍生物的合成。立体和区域特异性合成是在Schmidt糖基化条件下使用适当保护的L-rhamopyranosyl和D-glucopyranosylamine构建基块实现的。五糖的合成是通过[3 + 2]策略实现的，通过11个线性步骤，单糖结构单元10和14的总收率为5.2％。

  DOI：

  10.1016/j.carres.2017.11.010

文献信息

• Synthesis of the 6-deoxytalose-containing tri- and hexasaccharides of the O-antigen polysaccharide from Mesorhizobium huakuii IFO15243T
  作者：Guanghui Zong、Yichen Feng、Xiaomei Liang、Liezhong Chen、Jianjun Zhang、Daoquan Wang

  DOI：10.1016/j.carres.2010.07.023

  日期：2010.9

  huakuii IFO15243, has been accomplished through suitable protecting group manipulations and stereoselective glycosylation reactions starting from commercially available l-rhamnose. The target oligosaccharides in the form of their p-methoxyphenyl glycosides are suitable for further glycoconjugate formation via selective cleavage of this group.

  通过从商业上可获得的1-鼠李糖开始的合适的保护基团操纵和立体选择性糖基化反应，已经完成了由Husorhizobium huakuii IFO15243合成三糖和六糖（O-抗原多糖重复单元的单体和二聚体）的操作。对-甲氧基苯基糖苷形式的目标寡糖适合于通过选择性切割该基团而进一步形成糖缀合物。
• Synthesis of the repeating unit of O-specific polysaccharide isolated from the water-borne bacteria Aeromonas bestiarum 207
  作者：Yiren Xu、Guanghui Zong、Shuhui Jin、Jianjun Zhang

  DOI：10.1016/j.carres.2017.11.010

  日期：2018.2

  of OPS antigens from Aeromonas bestiarum was identified as pentasaccharide repeating units. Synthesis of the pentasaccharide repeating unit and its derivative are reported. Stereo- and regio-specific synthesis was achieved under Schmidt glycosylation conditions employing appropriately protected L-rhamopyranosyl and D-glucopyranosylamine building blocks. The pentasaccharide synthesis was achieved using

  Bestiarum 207气单胞菌是对水产养殖有严重影响的细菌病原体。在最近的研究中，来自气单胞菌的OPS抗原的结构被鉴定为五糖重复单元。报道了五糖重复单元及其衍生物的合成。立体和区域特异性合成是在Schmidt糖基化条件下使用适当保护的L-rhamopyranosyl和D-glucopyranosylamine构建基块实现的。五糖的合成是通过[3 + 2]策略实现的，通过11个线性步骤，单糖结构单元10和14的总收率为5.2％。
• 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.