methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate | 1158797-05-7

• 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-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate
• CAS: 1158797-05-7
• 化学式: C₅₆H₇₇Cl₆N₅O₁₉Si₂
• 分子量: 1393.14
• InChiKey: HZETUEGNRXPZNS-NXKADFAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.26
• 重原子数：
  88
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  264
• 氢给体数：
  3
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 2,3-di-O-benzoyl-4-[4,6-O-di-tert-butylsilylidene-3-O-levulinoyl-2-N-trichloroacetamido-β-D-glucopyranosyl]-1-thio-β-D-glucopyranosyl uronate) 、 methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate 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 2.5h， 以98%的产率得到methyl (2S,3S,4S,5R,6R)-3-[[(4aR,6S,7R,8R,8aS)-8-[(2R,3R,4S,5S,6S)-5-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-3,4-dibenzoyloxy-6-methoxycarbonyloxan-2-yl]oxy-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-(4-oxopentanoyloxy)-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate 在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 反应 0.25h， 以94%的产率得到methyl (2S,3S,4S,5R,6R)-6-[[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxy]-3-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-hydroxy-7-[(2,2,2-trichloroacetyl)amino]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-4,5-dibenzoyloxyoxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713

文献信息

• Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies
  作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo9003713

  日期：2009.6.5

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.