4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside | 848568-07-0

• 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-2-deoxy-β-D-glucopyranoside
• CAS: 848568-07-0
• 化学式: C₂₅H₃₉NO₁₃
• 分子量: 561.584
• InChiKey: WHHYEXCCQIYSGX-QSRLQAIUSA-N

物化性质

• 沸点：
  694.5±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.52
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  185.38
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.5h， 生成
  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：

  4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到4-pentenyl 3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-acetamido-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