benzyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside | 693219-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: benzyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: [(3aS,4R,6R,7R,7aS)-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-yl] acetate
• CAS: 693219-37-3
• 化学式: C₃₄H₄₂O₇Si
• 分子量: 590.789
• InChiKey: KCSPHKNEQLFEFI-UNKWROQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到benzyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-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 、 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 benzyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-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

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。