p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-mannopyranoside | 1002744-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS: 1002744-65-1
• 化学式: C₃₇H₄₀O₇
• 分子量: 596.72
• InChiKey: PCFCFUKSOUWFBG-DWCHZDDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-mannopyranoside 在 palladium dichloride 甲醇 作用下， 反应 3.0h， 以85%的产率得到4-methoxyphenyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside
  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-4,6-di-O-benzyl-α-D-mannopyranoside 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以91%的产率得到p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-α-D-mannopyranoside
  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

文献信息

• Synthesis of 8-azidooctyl glycoside derivatives of the O-chain repeating unit of Escherichia coli O9a lipopolysaccharide and a methylated analog
  作者：Dianjie Hou、Fredrik Skogman、Todd L. Lowary

  DOI：10.1016/j.carres.2008.02.025

  日期：2008.7

  Described is the synthesis of 8-azidooctyl glycoside derivatives of the Escherichia coli serotype O9a O-chain tetrasaccharide repeating unit and the terminal tetrasaccharide motif in this polysaccharide, which contains a methyl group on O-3 of the distal mannopyranose residue. The assembly of these compounds involved the sequential addition of monosaccharide residues from the reducing to the nonreducing end of the molecule using glycosyl trichloroacetimidate donors. Both compounds were initially prepared as p-methoxyphenyl glycosides, which were converted to the corresponding 8-azidooctyl derivatives at a late stage in the synthesis. (C) 2008 Elsevier Ltd. All rights reserved.