2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1194234-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS: 1194234-41-7
• 化学式: C₇₂H₉₂O₁₂
• 分子量: 1149.52
• InChiKey: AHKOAUWGOBDKMS-ZKRLLHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.74
• 重原子数：
  84.0
• 可旋转键数：
  37.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  118.6
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 20% Pd(OH)2/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以51%的产率得到2-hexyl-1-octyl 6-O-(4-O-isobutyryl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

  摘要：

  Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation Of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

  DOI：

  10.1021/jo901569v
• 作为产物：
  描述：

  dimethyl dihexylmalonate 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 三乙胺 、 lithium chloride 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 35.0h， 生成 2-hexyl-1-octyl 6-O-(2,3,6-tri-O-benzyl-4-O-isobutyryl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates

  摘要：

  Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation Of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

  DOI：

  10.1021/jo901569v