ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside | 1132975-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside
• 英文别名: ethyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-1-thio-α-D-mannopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-ethylsulfanyloxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 1132975-40-6
• 化学式: C₃₄H₄₁NO₁₇S
• 分子量: 767.762
• InChiKey: KNHZLLWSLYXUAP-JKWMQQGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  248
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside 、 O-(4,6-O-benzylidene-β-D-mannopyranosyl)-(1*4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1*4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-β-D-glucopyranosyl azide 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以88%的产率得到O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j
• 作为产物：
  描述：

  ethyl 6-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到ethyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j

文献信息

• Synthesis of a truncated bi-antennary complex-type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M
  作者：Thomas B. Parsons、James W. B. Moir、Antony J. Fairbanks

  DOI：10.1039/b907273j

  日期：——

  The synthesis of a truncated complex N-glycan hexasaccharide oxazoline was achieved producing a substrate that was assayed as an activated donor for glycosylation catalysed by the endohexosaminidases Endo A and Endo M. For Endo M competitive product hydrolysis was seen to limit synthetic efficiency. In spite of its natural hydrolytic selectivity wild type Endo A was able to process the truncated complex N-glycan oxazoline, albeit with limited synthetic efficiency; notably the product was not a substrate for Endo A catalysed hydrolysis. Two Endo A mutants, E173Q and E173H, were also assayed, but were unable to process this oxazoline.

  我们成功合成了一种截断的复杂N-糖苷六糖苷酸的噁唑啉，并将其作为底物进行评估，以用作由内糖胺酶Endo A和Endo M催化的糖基化反应的活化供体。对于Endo M，竞争性产物水解被观察到限制了合成效率。尽管天然的水解选择性较高，野生型Endo A仍能够处理这种截断的复杂N-糖苷噁唑啉，但合成效率有限；值得注意的是，所生成的产物并不是Endo A催化水解的底物。同时评估了两个Endo A突变体，E173Q和E173H，但它们无法处理该噁唑啉。