p-methylphenyl 2-deoxy-1-thio-6-O-triisopropylsilyl-D-galactopyranoside | 918334-12-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: p-methylphenyl 2-deoxy-1-thio-6-O-triisopropylsilyl-D-galactopyranoside
• 英文别名: (2R,3R,4R)-6-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxane-3,4-diol
• CAS: 918334-12-0
• 化学式: C₂₂H₃₈O₄SSi
• 分子量: 426.693
• InChiKey: AUFADHGKMHZWHM-LKCXNPEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-deoxy-1-thio-6-O-triisopropylsilyl-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三(2-氯乙基)胺 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 0.84h， 生成 2-azido-3,4-di-O-benzyl-1-O-triisopropylsilyl-octadec-6-ene
  参考文献：
  名称：

  Synthesis of α-Galactosyl Ceramide, a Potent Immunostimulatory Agent

  摘要：

  alpha-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of alpha-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.

  DOI：

  10.1021/jo0201530
• 作为产物：
  描述：

  三异丙基氯硅烷 、 p-methylphenyl 2-deoxy-1-thio-D-galactopyranoside 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以86%的产率得到p-methylphenyl 2-deoxy-1-thio-6-O-triisopropylsilyl-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of α-Galactosyl Ceramide, a Potent Immunostimulatory Agent

  摘要：

  alpha-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of alpha-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.

  DOI：

  10.1021/jo0201530

文献信息

• Synthesis of α-Galactosyl Ceramide, a Potent Immunostimulatory Agent
  作者：Oliver Plettenburg、Vera Bodmer-Narkevitch、Chi-Huey Wong

  DOI：10.1021/jo0201530

  日期：2002.6.1

  alpha-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of alpha-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.