methyl (2R)-3-O-tert-butyldiphenylsilyl-2-O-[4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-1-O-α-D-glucopyranosyl]-2,3-dihydroxypropanoate | 1448042-50-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R)-3-O-tert-butyldiphenylsilyl-2-O-[4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-1-O-α-D-glucopyranosyl]-2,3-dihydroxypropanoate
• CAS: 1448042-50-9
• 化学式: C₇₁H₈₀O₁₆Si
• 分子量: 1217.49
• InChiKey: ULMSIMOAUVLERT-YDOAZUBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.01
• 重原子数：
  88.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  171.2
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 、 methyl 3-tert-butyldiphenylsilyl-(2R)-2-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)glycerate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到methyl (2R)-3-O-tert-butyldiphenylsilyl-2-O-[4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-1-O-α-D-glucopyranosyl]-2,3-dihydroxypropanoate
  参考文献：
  名称：

  The effect of electron withdrawing protecting groups at positions 4 and 6 on 1,2-cis galactosylation

  摘要：

  Ethyl 2,3,4-O-tribenzyl-6-O-chloroacetyl-1-D-thiogalactoside, phenyl 4,6-O-diacetyl-2,3-dibenzyl-1-D-thiogalactoside and phenyl 2,3-O-dibenzyl-4,6-O-dichloroacetyl-1-D-thiogalactoside were employed in the study of the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered linear primary alcohols to other sugars, using NIS/TfOH as activator. Higher alpha-selectivities were obtained in the glycosylation reactions with phenyl 2,3-O-dibenzyl-4,6-O-dichloroacetyl-1-D-thiogalactoside as the donor, showing that a stronger electron withdrawing 4-O-ester group had an influence in the anomeric selectivity favouring the formation of 1,2-cis galactosides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.038