3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate | 946390-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-6-[(2S,3S,4S,5R,6R)-6-(3-azidopropoxy)-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxy-2-phenyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate
• CAS: 946390-62-1
• 化学式: C₆₀H₅₇Cl₃N₄O₂₂
• 分子量: 1292.49
• InChiKey: DLTFOZMFQFMVIT-KHMZTQQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  89
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  295
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-1-thio-β-D-glucopyranoside 、 3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate 在 二苯基亚砜 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以62%的产率得到methyl (2S,3S,4S,5R,6R)-3-[[(2R,4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(2R,4aR,6S,7R,8R,8aS)-8-(4-oxopentanoyloxy)-2-phenyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2-phenyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-(3-azidopropoxy)-4,5-dibenzoyloxyoxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers Using Ph₂SO/Tf₂O-Mediated Glycosylations

  摘要：

  The synthesis of hyaluronic acid (HA) oligomers using a stepwise glycosylation strategy is described. This method employs protected 1-hydroxyuronic acid and 1-phenylthio glucosamine donors, both of which are activated with the Ph2SO/Tf2O activator system.

  DOI：

  10.1021/jo070704s
• 作为产物：
  描述：

  3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate) 在 吡啶 、 二苯基亚砜 、 一水合肼 、 溶剂黄146 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-azidopropyl (methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(methyl (2,3-di-O-benzoyl-β-D-glucopyranosyl) uronate)-β-D-glucopyranosyl)-β-D-glucopyranosid) uronate
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers Using Ph₂SO/Tf₂O-Mediated Glycosylations

  摘要：

  The synthesis of hyaluronic acid (HA) oligomers using a stepwise glycosylation strategy is described. This method employs protected 1-hydroxyuronic acid and 1-phenylthio glucosamine donors, both of which are activated with the Ph2SO/Tf2O activator system.

  DOI：

  10.1021/jo070704s