(2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-6-phenylsulfanyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine | 196697-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-6-phenylsulfanyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 196697-67-3
• 化学式: C₂₉H₃₀O₅S
• 分子量: 490.62
• InChiKey: XWNHUBPKIOQAJA-SDPIAUFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-6-phenylsulfanyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 在 甲醇 、 {Ir(COD)[PCH₃(C₆H₅)2]}PF₆ 、 camphor-10-sulfonic acid 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 phenyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  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：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 sodium hydroxide 、 四丁基硫酸氢铵 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-6-phenylsulfanyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
  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

• Shao; Guo, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 297 - 307
  作者：Shao、Guo

  DOI：——

  日期：——
• 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.