2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-beta-D-glucopyranoside | 338971-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-beta-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[2-(2-azidoethoxy)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 338971-32-7
• 化学式: C₁₂H₂₂N₄O₇
• 分子量: 334.329
• InChiKey: YIYBKMXLQSWSPH-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-beta-D-glucopyranoside 在 barium dihydroxide 、 sodium cyanoborohydride 、 zinc(II) chloride 、 barium(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.25h， 生成
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459
• 作为产物：
  描述：

  1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(2-Azidoethoxy)ethyl-2-acetamido-2-deoxy-beta-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459

文献信息

• Efficient Preparation of Natural and Synthetic Galactosides with a Recombinant β-1,4-Galactosyltransferase-/UDP-4‘-Gal Epimerase Fusion Protein
  作者：Ola Blixt、Jillian Brown、Melissa J. Schur、Warren Wakarchuk、James C. Paulson

  DOI：10.1021/jo0057809

  日期：2001.4.1

  galactose to a variety of different glucose- and glucosamine-containing acceptors, and utilizes either UDP-galactose or UDP-glucose as donor substrates. A crude lysate from Escherichia coli expressing the fusion protein is demonstrated to be sufficient for the efficient preparation of galactosylated oligosaccharides from inexpensive UDP-glucose in a multigram scale. Lysates containing the fusion protein are

  基于LacNAc的寡糖的多种生物学作用导致对生物学研究的这些结构的需求增加。在该报告中，描述了使用细菌β-4-半乳糖基转移酶/ -UDP-4'-gal-表异构酶融合蛋白合成β-半乳糖苷的有效途径。将来自脑膜炎奈瑟氏球菌的lgtB基因和来自嗜热链球菌的galE基因融合并克隆到表达载体pCW中。融合蛋白将半乳糖转移至各种不同的含葡萄糖和葡萄糖胺的受体，并利用UDP-半乳糖或UDP-葡萄糖作为供体底物。已证明表达融合蛋白的大肠杆菌的粗裂解物足以以毫克规模从廉价的UDP葡萄糖有效制备半乳糖基化的寡糖。还发现含有融合蛋白的裂解物可用于在偶联的反应混合物中产生更复杂的寡糖，例如，用于由N-乙酰基葡糖胺制备唾液酸化物。因此，细菌表达的融合蛋白非常适合于方便，经济地制备天然低聚糖和基于乳糖胺核心的合成衍生物。
• Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups
  作者：Santiago Figueroa Pérez、Raul González Lio、Violeta Fernández Santana、Vicente Verez Bencomo

  DOI：10.1080/07328309808007459

  日期：1998.8.1

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.