N-[(2S,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7S,8S,8aR)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide | 539836-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7S,8S,8aR)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide
• CAS: 539836-16-3
• 化学式: C₈₆H₉₈N₂O₁₉S₂Si
• 分子量: 1555.94
• InChiKey: VUWHQFXCNGGXBK-JCPYZXPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.55
• 重原子数：
  110
• 可旋转键数：
  35
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  248
• 氢给体数：
  2
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7S,8S,8aR)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 以25 g的产率得到N-[(2S,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7S,8S,8aS)-8-hydroxy-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Toward a Prostate Specific Antigen-Based Prostate Cancer Diagnostic Assay: Preparation of Keyhole Limpet Hemocyanin -Conjugated Normal and Transformed Prostate Specific Antigen Fragments

  摘要：

  Prostate specific antigen (PSA) molecules secreted by cancerous and normal prostate cells differ in their N-linked glycan composition, while the peptide backbone appears to be conserved. Antibodies selectively recognizing such differentially glycosylated PSA structures could form a basis for a new diagnostic assay for prostate cancer. Twenty-amino acid PSA fragments carrying di-, tri-, and tetrabranched complex-type glycans were prepared by total synthesis and conjugated to maleimide-modified keyhole limpet hemocyanin (KLH) carrier protein through backbone Cys residues. These glycopeptide/KLH conjugates were then used for antibody generation.

  DOI：

  10.1021/ja8028137
• 作为产物：
  描述：

  [(2R,4aR,6R,7S,8S,8aR)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] trifluoromethanesulfonate 、 N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide 以 二氯甲烷 为溶剂， 生成 N-[(2S,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7S,8S,8aR)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-[(2R,3S,4R,5R,6R)-5-(benzenesulfonamido)-6-[tert-butyl(dimethyl)silyl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]benzenesulfonamide 、
  参考文献：
  名称：

  Toward a Prostate Specific Antigen-Based Prostate Cancer Diagnostic Assay: Preparation of Keyhole Limpet Hemocyanin -Conjugated Normal and Transformed Prostate Specific Antigen Fragments

  摘要：

  Prostate specific antigen (PSA) molecules secreted by cancerous and normal prostate cells differ in their N-linked glycan composition, while the peptide backbone appears to be conserved. Antibodies selectively recognizing such differentially glycosylated PSA structures could form a basis for a new diagnostic assay for prostate cancer. Twenty-amino acid PSA fragments carrying di-, tri-, and tetrabranched complex-type glycans were prepared by total synthesis and conjugated to maleimide-modified keyhole limpet hemocyanin (KLH) carrier protein through backbone Cys residues. These glycopeptide/KLH conjugates were then used for antibody generation.

  DOI：

  10.1021/ja8028137

文献信息

• Toward a Prostate Specific Antigen-Based Prostate Cancer Diagnostic Assay: Preparation of Keyhole Limpet Hemocyanin -Conjugated Normal and Transformed Prostate Specific Antigen Fragments
  作者：Vadim Y. Dudkin、Justin S. Miller、Anna S. Dudkina、Christophe Antczak、David A. Scheinberg、Samuel J. Danishefsky

  DOI：10.1021/ja8028137

  日期：2008.10.15

  Prostate specific antigen (PSA) molecules secreted by cancerous and normal prostate cells differ in their N-linked glycan composition, while the peptide backbone appears to be conserved. Antibodies selectively recognizing such differentially glycosylated PSA structures could form a basis for a new diagnostic assay for prostate cancer. Twenty-amino acid PSA fragments carrying di-, tri-, and tetrabranched complex-type glycans were prepared by total synthesis and conjugated to maleimide-modified keyhole limpet hemocyanin (KLH) carrier protein through backbone Cys residues. These glycopeptide/KLH conjugates were then used for antibody generation.