(3aR,4R,6R,7R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4-(octyloxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol | 958229-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,6R,7R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4-(octyloxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 958229-35-1
• 化学式: C₂₃H₄₆O₆Si
• 分子量: 446.7
• InChiKey: VSTGUBQVPBTWDS-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6R,7R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4-(octyloxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol 、 Benzyloxycarbonyl-L-phenylalanin-anhydrid 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 octyl 4-O-((S)-2-benzyloxycarbonylamino-3-phenylpropanoyl)-β-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：

  n-辛基-β-D-吡喃葡萄糖苷 在 咪唑 、 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3aR,4R,6R,7R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4-(octyloxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol 、 (3aR,4R,6R,7R,7aR)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-6-(octyloxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol
  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