4-Oxo-pentanoic acid (2S,4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester | 179072-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Oxo-pentanoic acid (2S,4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS: 179072-57-2
• 化学式: C₂₄H₂₆O₇S
• 分子量: 458.532
• InChiKey: KYGRPNYUEYXLIN-QJKCBQBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2S,4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 calcium sulfate 、 N-碘代丁二酰亚胺 、 二氯二茂铪 、 silver trifluoromethanesulfonate 、 silver perchlorate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

  摘要：

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00901-x
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.33h， 生成 4-Oxo-pentanoic acid (2S,4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
  参考文献：
  名称：

  Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

  摘要：

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00901-x

文献信息

• Discovery of Oligosaccharide Antigens for Semi‐Synthetic Glycoconjugate Vaccine Leads against <i>Streptococcus suis</i> Serotypes 2, 3, 9 and 14**
  作者：Shuo Zhang、Mauro Sella、Julinton Sianturi、Patricia Priegue、Dacheng Shen、Peter H. Seeberger

  DOI：10.1002/anie.202103990

  日期：2021.6.21

  Streptococcus suis bacteria are one of the most serious health problems for pigs and an emerging zoonotic agent in humans working in the swine industry. S. suis bacteria express capsular polysaccharides (CPS) a major bacterial virulence factor that define the serotypes. Oligosaccharides resembling the CPS of S. suis serotypes 2, 3, 9, and 14 have been synthesized, glycans related to serotypes 2 and

  猪链球菌是猪最严重的健康问题之一，也是养猪业人类中新出现的人畜共患病病原体。猪链球菌表达荚膜多糖（CPS），这是定义血清型的主要细菌毒力因子。类似于猪链球菌血清型 2、3、9 和 14 的 CPS 的寡糖已被合成，与血清型 2 和 9 相关的聚糖被放置在聚糖阵列表面上以筛选来自受感染猪的血液。以这种方式鉴定了用于开发半合成猪链球菌血清型 2 和 9 糖复合兽用疫苗的先导抗原。