6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranose | 1352442-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranose
• CAS: 1352442-64-8
• 化学式: C₂₃H₃₆O₇Si
• 分子量: 452.62
• InChiKey: BZTQXUFEGBDHSP-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  allyl 3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranoside 在 吡啶 、 甲醇 、 sodium hydride 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.17h， 生成 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranose 、 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranose
  参考文献：
  名称：

  Glycosylation studies on conformationally restricted 3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation

  摘要：

  Conformationally restricted 3,5-O-di-tert-butylsilylene-D-galactofuranosyl trichloroacetimidate donors were synthesized from allyl alpha-D-galactofuranoside for the construction of 1,2-cis alpha-D-galactofuranosyl linkages. Glycosylation reactions were performed with several acceptors, including D-galactono-1,4-lactone, D-rhamnopyranosyl, and D-mannopyranosyl derivatives. The influence of the temperature and the reaction solvents was evaluated, as well as the 6-O-substitution pattern of the donor. The higher alpha-selectivities were obtained at -78 degrees C in diethyl ether as solvent. 6-O-Acetyl substitution on constrained donor increased the alpha-selectivity compared to the 6-O-benzyl substitution. Almost no selectivities were observed in the non-participating solvent CH2Cl2. In contrast, ethereal solvents enhanced the alpha-selectivity suggesting a participating effect in the reaction intermediate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.004