phenyl 1-thio-2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-β-D-galactopyranoside | 1176030-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 1-thio-2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: phenyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside
• CAS: 1176030-73-1
• 化学式: C₂₃H₂₈O₆S
• 分子量: 432.538
• InChiKey: KCVLPWYISREONK-CTWRKMMKSA-N

物化性质

• 沸点：
  575.6±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 1-thio-2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 生成 allyl 3,4-di-O-benzoyl-6-O-benzyl-2-O-p-methoxybenzyl-α-D-galactopyranosyl-(1-3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach

  摘要：

  To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (27) and hexasaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.005
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.17h， 生成 phenyl 1-thio-2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach

  摘要：

  To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (27) and hexasaccharide propyl alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-D-galactopyranosyl-(1 -> 3)-alpha-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.005

文献信息

• Facile synthesis of biotin-labelled α-galactosylceramide as antigen for invariant natural killer T cells
  作者：Chengfeng Xia、Wenpeng Zhang、Yalong Zhang、Robert L. Woodward、Jinhua Wang、Peng G. Wang

  DOI：10.1016/j.tet.2009.06.007

  日期：2009.8

  When iNKT cells are stimulated by the CD1d presented exogenous alpha-galactosylceramide, a myriad of cytokines are released that trigger a variety of immune responses. However, the invisibility and poor aqueous Solubility of alpha-galactosylceramide during bioassays have rendered it difficult to study the aforementioned biological responses. Accordingly, a biotin-labelled alpha-galactosylceramide was prepared to facilitate detection of this antigen in the immune process. The problematic low solubility was also remedies via incorporation of a truncated acyl chain. (C) 2009 Elsevier Ltd. All rights reserved.