O-(2,6-di-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate | 1352442-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,6-di-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate
• 英文别名: [(4R,4aS,6S,7R,7aS)-2,2-ditert-butyl-7-phenylmethoxy-4-(phenylmethoxymethyl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl] 2,2,2-trichloroethanimidate
• CAS: 1352442-67-1
• 化学式: C₃₀H₄₀Cl₃NO₆Si
• 分子量: 645.095
• InChiKey: XJXQKXADVRFVIN-CAKRBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-(2,6-di-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate 、 环己醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 0.67h， 以71%的产率得到cyclohexyl 2,6-di-O-benzyl-3,5-O-(di-tertbutylsilanediyl)-α-D-galactofuranoside
  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
• 作为产物：
  描述：

  二叔丁基硅基双(三氟甲烷磺酸) 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 10.84h， 生成 O-(2,6-di-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate
  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

文献信息

• Glycosylation studies on conformationally restricted 3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation
  作者：Mariano J. Tilve、Carola Gallo-Rodriguez

  DOI：10.1016/j.carres.2011.10.004

  日期：2011.10

  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.