methyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside | 1352442-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-β-D-galactofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• 英文别名: methyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tertbutylsilanediyl)-β-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6S)-2-[[(4R,4aS,6R,7R,7aS)-4-(acetyloxymethyl)-2,2-ditert-butyl-7-phenylmethoxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 1352442-77-3
• 化学式: C₅₁H₆₀O₁₅Si
• 分子量: 941.114
• InChiKey: PALXUYQGWDXWLP-MSCRRXHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 、 O-(6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-D-galactofuranosyl)trichloroacetimidate 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84%的产率得到methyl 6-O-acetyl-2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-galactofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  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