O-(6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate | 1352442-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(6-O-acetyl-2-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-6-(2,2,2-trichloroethanimidoyl)oxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-4-yl]methyl acetate
• CAS: 1352442-65-9
• 化学式: C₂₅H₃₆Cl₃NO₇Si
• 分子量: 597.008
• InChiKey: VGKPYWQEOYWGBB-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 O-(6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl)trichloroacetimidate 、 O-(6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-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