6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside | 1392400-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS: 1392400-69-9
• 化学式: C₁₀₅H₁₂₄Cl₄N₂O₂₇
• 分子量: 1987.95
• InChiKey: ZOGKTHSNNJJDGU-NBUIQVGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.66
• 重原子数：
  138.0
• 可旋转键数：
  44.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  312.47
• 氢给体数：
  2.0
• 氢受体数：
  27.0

反应信息

• 作为产物：
  描述：

  6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside 、 1-硫-乙基-2,3,4-三-氧-苄基-b-L-硫代呋喃岩藻糖苷 在 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以31%的产率得到6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Matched and mismatched acceptor/donor pairs in the glycosylation of a trisaccharide diol free at O-3 of two N-acylated glucosamine residues

  摘要：

  Reciprocal donor acceptor selectivity (RDAS) and double diastereodifferentiation are two concepts that have been used to explain how a glycosyl acceptor and donor may be 'matched' or 'mismatched' in glycosylation reactions. We describe here how the alpha-L-fucosylation and beta-D-galactosylation of a trisaccharide displaying two equatorial OH groups at C-3 of N-acylated glucosamine units led to different regioselectivities or different 'matched' pairs. These results may be explained under the reciprocal donor acceptor selectivity or double diastereodifferentiation concepts. We also suggest a third explanation to these results: the presence of a benzylidene at the nonreducing end acceptor led to rigidity at this residue which resulted into a mismatched pair during beta-D-galactosylation but allowed alpha-L-fucosylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.04.020