3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-2-trichloroacetamido-β-D-glucopyranoside | 1158797-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-2-trichloroacetamido-β-D-glucopyranoside
• 英文别名: N-[(4aR,6R,7R,8R,8aS)-6-(3-azidopropoxy)-2,2-ditert-butyl-8-hydroxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-7-yl]-2,2,2-trichloroacetamide
• CAS: 1158797-02-4
• 化学式: C₁₉H₃₃Cl₃N₄O₆Si
• 分子量: 547.939
• InChiKey: RKUXVTMEVJQMPL-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-2-trichloroacetamido-β-D-glucopyranoside 、 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) 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 以75%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-(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
  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：

  3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 反应 0.25h， 以85%的产率得到3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-2-trichloroacetamido-β-D-glucopyranoside
  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.