4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside | 583041-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: p-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside
• CAS: 583041-01-4
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: AXPGJTSNVHYDPJ-IPAQOYIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 氢气 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 、 碳酸氢钠 、 乙二胺 、 硫脲 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 98.0h， 生成 4-methoxyphenyl 2-acetamido-2-deoxy-α-L-fucopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480
• 作为产物：
  描述：

  4-methoxyphenyl 2,3,4-tetra-O-acetyl-α-L-rhamnopyranoside 在 吡啶 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4-methoxyphenyl 4-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480

文献信息

• Practical preparation of 2-azido-2-deoxy-β-d-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides
  作者：Jianjun Zhang、Shiqiang Yan、Xiaomei Liang、Jingping Wu、Daoquan Wang、Fanzuo Kong

  DOI：10.1016/j.carres.2007.09.001

  日期：2007.12

  1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-beta-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-beta-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative

  从相应的化合物制备1-O-烯丙氧羰基（或乙氧羰基）-2-叠氮基-2-脱氧-3-O-苄基（或烯丙基或苯甲酰基）-4，6-O-异亚丙基-β-d-甘露吡喃糖衍生物。通过2-羟基的三氟甲磺酸化和随后的叠氮化物离子取代SN2，可以高产率地生成2-羟基-β-d-吡喃葡萄糖基碳酸酯。使用这些衍生物有效地合成了含有N-乙酰基-甘露糖胺的三糖，其是鲍曼不动杆菌推定的O10抗原的片段。
• 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.