benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside | 141410-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: (3aS,4R,6R,7R,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-6-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 141410-44-8
• 化学式: C₃₂H₄₀O₆Si
• 分子量: 548.751
• InChiKey: DPKDSNYCRIFVTK-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 Dowex DR-2030 H⁽¹⁺⁾-form 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 benzyl 2-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Selectively protected galactose derivatives for the synthesis of branched oligosaccharides

  摘要：

  Synthesis and characterization of several new anomerically pure galactose derivatives, based on simple and effective protective group manipulations of benzyl beta-D-galactopyranoside, are reported. The monosaccharides described contain selectively protected/deprotected hydroxyl functionalities at their 1,2,3,4- and 6-positions rendering them useful as building blocks for construction of branched oligosaccharides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.054
• 作为产物：
  描述：

  苄基Beta-D-吡喃半乳糖苷 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 生成 benzyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成

  摘要：

  New-to-Nature D-半乳糖基溶血磷脂经过合理设计和合成，可作为磷脂酰肌醇磷酸激酶的人工底物和非 ATP 竞争性抑制剂，磷脂酰肌醇磷酸激酶是经过验证的致命人类疾病（包括癌症、肌萎缩侧索硬化和 SARS- COVID-2 感染。D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成（X. Huang、J. Hu 等人）

  DOI：

  10.1002/chem.202202083

文献信息

• Acyl Group Migration and Cleavage in Selectively Protected β-<scp>d</scp>-Galactopyranosides as Studied by NMR Spectroscopy and Kinetic Calculations
  作者：Mattias U. Roslund、Olli Aitio、Johan Wärnå、Hannu Maaheimo、Dmitry Yu. Murzin、Reko Leino

  DOI：10.1021/ja801177s

  日期：2008.7.1

  protective groups and their relative stabilities at variable pH for a series of beta- d-galactopyranoses were studied by NMR spectroscopy. The clockwise and counterclockwise migration rates for the different ester groups were accurately determined by use of a kinetic model. The results presented provide new insights into the acid and base stabilities of commonly used ester protecting groups and the phenomenon

  通过NMR光谱研究了一系列β-d-吡喃半乳糖的乙酰基、新戊酰基和苯甲酰基保护基团的迁移及其在可变pH下的相对稳定性。不同酯基的顺时针和逆时针迁移速率通过使用动力学模型准确确定。所呈现的结果为常用酯保护基团的酸碱稳定性和酰基迁移现象提供了新的见解，并可能有助于规划合成策略。
• Radical cyclisation of hept-1-enitols
  作者：Hartmut Redlich、Wolfgang Sudau、Anna Katrin Szardenings、Roland Vollerthun

  DOI：10.1016/0008-6215(92)84055-w

  日期：1992.3

  7-Deoxy-7-iodohept-1-enitols react intramolecularly to give 5-carba analogues of pyranoses (pseudo sugars) by the action of tributyltin hydride, which generates a radical at C-7. The configuration at the new chiral centre depends on the relative orientation of the oxygen functions in the starting material and the pattern of substitution.
• Selectively protected galactose derivatives for the synthesis of branched oligosaccharides
  作者：Reko L Lehtilä、Juho O Lehtilä、Mattias U Roslund、Reko Leino

  DOI：10.1016/j.tet.2004.02.054

  日期：2004.4

  Synthesis and characterization of several new anomerically pure galactose derivatives, based on simple and effective protective group manipulations of benzyl beta-D-galactopyranoside, are reported. The monosaccharides described contain selectively protected/deprotected hydroxyl functionalities at their 1,2,3,4- and 6-positions rendering them useful as building blocks for construction of branched oligosaccharides. (C) 2004 Elsevier Ltd. All rights reserved.
• Rational Design and Synthesis of D‐galactosyl Lysophospholipids as Selective Substrates and non‐ATP‐competitive Inhibitors of Phosphatidylinositol Phosphate Kinases
  作者：Mengxia Sun、Chi Zhang、Dexin Sui、Canchai Yang、Dohun Pyeon、Xuefei Huang、Jian Hu

  DOI：10.1002/chem.202202083

  日期：2023.1.9

  and non-ATP-competitive inhibitors of phosphatidylinositol phosphate kinases, which are validated drug targets for deadly human diseases including cancers, amyotrophic lateral sclerosis, and SARS-COVID-2 infection. Rational Design and Synthesis of D-galactosyl Lysophospholipids as Selective Substrates and non-ATP-competitive Inhibitors of Phosphatidylinositol Phosphate Kinases (X. Huang, J. Hu et al

  New-to-Nature D-半乳糖基溶血磷脂经过合理设计和合成，可作为磷脂酰肌醇磷酸激酶的人工底物和非 ATP 竞争性抑制剂，磷脂酰肌醇磷酸激酶是经过验证的致命人类疾病（包括癌症、肌萎缩侧索硬化和 SARS- COVID-2 感染。D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成（X. Huang、J. Hu 等人）