p-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside | 500217-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside
• 英文别名: p-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside；4-methoxyphenyl 3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-3)[Bz(-2)][Bz(-4)][Bz(-6)]Man(a)-O-Ph(4-OMe)；[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5S,6R)-3,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(4-methoxyphenoxy)oxan-4-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 500217-05-0
• 化学式: C₆₈H₅₆O₁₉
• 分子量: 1177.18
• InChiKey: NHRTZONRKDUFOA-IAGHACIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  87
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  230
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以82%的产率得到
  参考文献：
  名称：

  Synthesis of the ‘primer–adaptor’ trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide

  摘要：

  Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)(8)N-3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.020
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside 在 palladium dichloride 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 p-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-3)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  α-（1→3）-连接的六氢己酸和甘露聚糖的高效实用合成

  摘要：

  α-（1→3）-连接的甘露六糖和甘露糖八糖作为其甲基糖苷是由相应的α-（1→3）-连接的二-（9）和四糖供体（21）与四糖受体（23）缩合而合成的分别进行脱酰作用。分别通过激活四糖20的C-1和四糖22的脱甲酰作用容易地制备供体21和受体23。通过将9与11偶联获得的19的1-Op-甲氧基苯基的氧化裂解制备四糖20。通过供体13与受体18的缩合获得四糖22。这些二糖9、11、13 ，使用对甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（1）和2,3,4通过简单的化学转化即可轻松制得18和

  DOI：

  10.1081/car-120014899

文献信息

• Synthesis of a derivative of a pentasaccharide repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3 as a benzoylated 2-methoxycarbonylethyl thioglycoside
  作者：P. I. Abronina、K. I. Galkin、L. V. Backinowsky、A. A. Grachev

  DOI：10.1007/s11172-010-0033-3

  日期：2009.2

  Block synthesis of a fully benzoylated derivative of the pentasaccharide α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-SCH2CH2CO2Me, the glycoside of the repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3, was performed.

  合成一种完全苯甲酰化的五糖衍生物α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp-SCH2CH2CO2Me，该衍生物是细菌肺炎克雷伯菌O3型O抗原多糖重复单元的糖苷。
• Synthesis of the ‘primer–adaptor’ trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide
  作者：Chunjuan Liu、Fredrik Skogman、Ye Cai、Todd L. Lowary

  DOI：10.1016/j.carres.2007.08.020

  日期：2007.12

  Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)(8)N-3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates. (C) 2007 Elsevier Ltd. All rights reserved.
• AN EFFICIENT AND PRACTICAL SYNTHESIS OF α-(1→3)-LINKED MANNOHEXAOSE AND MANNOOCTAOSE
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1081/car-120014899

  日期：2002.1.10

  tetrasaccharide 22, respectively. The tetrasaccharide 20 was prepared from oxidative cleavage of 1-O-p-methoxyphenyl of 19, which was obtained from coupling of 9 with 11. The tetrasaccharide 22 was obtained from condensation of the donor 13 with the acceptor 18. These disaccharides 9, 11, 13, and 18 were produced easily by simple chemical transformation using p-methoxyphenyl 3-O-allyl-α-d-mannopyranoside (1) and

  α-（1→3）-连接的甘露六糖和甘露糖八糖作为其甲基糖苷是由相应的α-（1→3）-连接的二-（9）和四糖供体（21）与四糖受体（23）缩合而合成的分别进行脱酰作用。分别通过激活四糖20的C-1和四糖22的脱甲酰作用容易地制备供体21和受体23。通过将9与11偶联获得的19的1-Op-甲氧基苯基的氧化裂解制备四糖20。通过供体13与受体18的缩合获得四糖22。这些二糖9、11、13 ，使用对甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（1）和2,3,4通过简单的化学转化即可轻松制得18和