2-[(2S,3R,4R,5S,6R)-5-[(4aR,6S,7S,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione | 512171-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4R,5S,6R)-5-[(4aR,6S,7S,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 512171-16-3
• 化学式: C₅₆H₆₂FNO₁₁Si
• 分子量: 972.192
• InChiKey: NDOFLZKDCHVFDU-GATMZJTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  70
• 可旋转键数：
  15
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-[(2S,3R,4R,5S,6R)-5-[(4aR,6S,7S,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 2.0h， 以96%的产率得到[(4aR,6S,7S,8S,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-6-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] acetate
  参考文献：
  名称：

  Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin

  摘要：

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.

  DOI：

  10.1021/ja021288q
• 作为产物：
  描述：

  methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 2-[(2S,3R,4R,5S,6R)-5-[(4aR,6S,7S,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin

  摘要：

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.

  DOI：

  10.1021/ja021288q

文献信息

• Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin
  作者：Ichiro Matsuo、Megumi Wada、Shino Manabe、Yoshiki Yamaguchi、Keisuke Otake、Koichi Kato、Yukishige Ito

  DOI：10.1021/ja021288q

  日期：2003.3.1

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.