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 | 201789-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 201789-48-2
• 化学式: C₄₂H₅₈O₁₈
• 分子量: 850.912
• InChiKey: SJRJUFUSWPKNQI-JZSZWRRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  60
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  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 碳酸氢钠 、 lithium iodide 作用下， 以 吡啶 为溶剂， 反应 5.0h， 以908 mg的产率得到Lithium; (2S,3S,4S,5R,6R)-6-((2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-allyloxy-5-benzoyloxy-tetrahydro-pyran-4-yloxy)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylate
  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：

  allyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 三氟乙酸 作用下， 反应 73.0h， 生成 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
  参考文献：
  名称：

  Kornilov; Kononov; Zatonskii, Russian Journal of Bioorganic Chemistry, 1997, vol. 23, # 8, p. 597 - 607

  摘要：

  DOI：

文献信息

• Kononov; Kornilov; Sherman, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 537 - 550
  作者：Kononov、Kornilov、Sherman、Zyryanov、Zatonsky、Shashkov、Nifant'ev

  DOI：——

  日期：——