octyl 4-O-((R)-2-benzyloxycarbonylamino-3-phenylpropanoyl)-β-D-glucopyranoside | 1194234-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: octyl 4-O-((R)-2-benzyloxycarbonylamino-3-phenylpropanoyl)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-octoxyoxan-3-yl] (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1194234-23-5
• 化学式: C₃₁H₄₃NO₉
• 分子量: 573.684
• InChiKey: YNQFHTPWYJFSMI-PMELEAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Z-D-phenylalanine anhydride 、 n-辛基-β-D-吡喃葡萄糖苷 在 2,4,6-三甲基吡啶 、 (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octoxyoxan-2-yl]methyl (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate 、 octyl 4-O-((R)-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

文献信息

• Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates
  作者：Yoshihiro Ueda、Wataru Muramatsu、Kenji Mishiro、Takumi Furuta、Takeo Kawabata

  DOI：10.1021/jo901569v

  日期：2009.11.20

  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.