phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside | 848568-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside
• CAS: 848568-10-5
• 化学式: C₂₇H₃₀O₈S
• 分子量: 514.596
• InChiKey: NFTWHTBJFBGXIL-JEMXKHELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 3,4-di-O-acetyl-6-O-benzoyl-2-O-levulinoyl-α-D-galactopyranose
  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：

  phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside
  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