4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside | 848568-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside
• CAS: 848568-08-1
• 化学式: C₃₂H₄₃NO₁₄
• 分子量: 665.692
• InChiKey: RRJPDOQGQJLZSH-ZWSBIGMKSA-N

物化性质

• 沸点：
  759.6±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  191.45
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  O-(3,4-di-O-acetyl-6-O-benzoyl-2-O-levulinoyl-D-galactopyranosyl)trichloroacetimidate 、 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以48%的产率得到
  参考文献：
  名称：

  Synthesis of a Ley neoglycoconjugate and Ley-functionalized gold glyconanoparticles

  摘要：

  The thiol functionalized Le(v) neoglycoconjugate 1 has been synthesized and used to prepare the Le(v)-functionalized gold glyconanoparticle 2. The synthesis of 1 has been carried out using a stepwise glycosylation strategy in which a suitably protected D-glucosamine derivative has been sequentially glycosylated at position 3 and then at position 4 with conveniently protected alpha-L-fucopyranosyl and beta-D-galactopyranosyl donors, respectively. The galactosylation step afforded the imidate 16 when the glycosyl acceptor contained a N-acetyglucosamine unit and the desired 4-O-galactopyranosyl derivative when the amino function protected as phthalimido group. The gold glyconanoparticle 2 has been prepared from 1 and has been characterized by NMR spectroscopy and transmission electron microscopy (TEM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.066
• 作为产物：
  描述：

  N-[(4aR,6R,7R,8R,8aS)-6-Pent-4-enyloxy-2-phenyl-8-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 在 吡啶 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Ley neoglycoconjugate and Ley-functionalized gold glyconanoparticles

  摘要：

  The thiol functionalized Le(v) neoglycoconjugate 1 has been synthesized and used to prepare the Le(v)-functionalized gold glyconanoparticle 2. The synthesis of 1 has been carried out using a stepwise glycosylation strategy in which a suitably protected D-glucosamine derivative has been sequentially glycosylated at position 3 and then at position 4 with conveniently protected alpha-L-fucopyranosyl and beta-D-galactopyranosyl donors, respectively. The galactosylation step afforded the imidate 16 when the glycosyl acceptor contained a N-acetyglucosamine unit and the desired 4-O-galactopyranosyl derivative when the amino function protected as phthalimido group. The gold glyconanoparticle 2 has been prepared from 1 and has been characterized by NMR spectroscopy and transmission electron microscopy (TEM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.066