p-methylphenyl 2,3,4-tri-O-benzoyl-6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-1-thio-β-D-glucopyranoside | 1128075-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3,4-tri-O-benzoyl-6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl-di(propan-2-yl)silyl]oxymethyl]-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1128075-41-1
• 化学式: C₅₀H₄₇F₁₇O₈SSi
• 分子量: 1159.04
• InChiKey: DAMWJBSPSYPYAW-DSJFEKNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.67
• 重原子数：
  77
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,3,4-tri-O-benzoyl-6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-1-thio-β-D-glucopyranoside 、 三氯乙腈 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以76%的产率得到2,3,4-tri-O-benzoyl-6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis and Applications of a Light-Fluorous Glycosyl Donor

  摘要：

  A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.

  DOI：

  10.1021/jo9000993
• 作为产物：
  描述：

  (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilane 、 p-tolyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 、 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以98.9%的产率得到p-methylphenyl 2,3,4-tri-O-benzoyl-6-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Applications of a Light-Fluorous Glycosyl Donor

  摘要：

  A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.

  DOI：

  10.1021/jo9000993

文献信息

• Synthesis and Applications of a Light-Fluorous Glycosyl Donor
  作者：Fa Zhang、Wei Zhang、Yan Zhang、Dennis P. Curran、Gang Liu

  DOI：10.1021/jo9000993

  日期：2009.3.20

  A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.