2-azidoethyl β-D-glucopyranosyluronic acid)-(1-> 3)-β-D-galactopyranoside | 321746-80-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl β-D-glucopyranosyluronic acid)-(1-> 3)-β-D-galactopyranoside
• CAS: 321746-80-9
• 化学式: C₁₄H₂₃N₃O₁₂
• 分子量: 425.35
• InChiKey: LDAPOHFZAFUCEA-MBAGJIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.97
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  244.36
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-azidoethyl β-D-glucopyranosyluronic acid)-(1-> 3)-β-D-galactopyranoside 在 乙酸酐 作用下， 反应 1.0h， 生成 (1S,3R,4R,5S,8S)-3-[(2R,3R,4S,5S,6R)-2-(2-Azido-ethoxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4,8-dihydroxy-2,6-dioxa-bicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

  摘要：

  The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta, 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta, and GlcA(beta -1 --> 3)Gal(beta were also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00258-5
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[(2R,3S,4S,5R,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-prop-2-enoxyoxan-4-yl]oxy-3,4,5-tris(2,2-dimethylpropanoyloxy)oxane-2-carboxylate 在 lithium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 18-冠醚-6 、 碳酸氢钠 、 臭氧 、 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 104.0h， 生成 2-azidoethyl β-D-glucopyranosyluronic acid)-(1-> 3)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

  摘要：

  The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta, 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta, and GlcA(beta -1 --> 3)Gal(beta were also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00258-5