3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside | 1158797-01-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside
• 英文别名: [(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] 4-oxopentanoate
• CAS: 1158797-01-3
• 化学式: C₂₄H₃₉Cl₃N₄O₈Si
• 分子量: 646.04
• InChiKey: RVCAYVJVZIYWNT-YHUYVZNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-叠氮基丙醇 、 4,6-O-di(tert-butyl)silylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到3-azidopropyl 4,6-O-di(tert-butyl)silylidene-1,2-dideoxy-3-O-levulinoyl-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.