isopropyl 4,6-O-benzylidene-2,3-di-O-(N-tert-butoxycarbonyl-L-alanyl)-α-D-glucopyranoside | 460354-51-2

• 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: isopropyl 4,6-O-benzylidene-2,3-di-O-(N-tert-butoxycarbonyl-L-alanyl)-α-D-glucopyranoside
• CAS: 460354-51-2
• 化学式: C₃₂H₄₈N₂O₁₂
• 分子量: 652.739
• InChiKey: IQNWYZLNNKEMDG-YARZBBGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  166.18
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  isopropyl 4,6-O-benzylidene-2,3-di-O-(N-tert-butoxycarbonyl-L-alanyl)-α-D-glucopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以64%的产率得到isopropyl 2,3-di-O-(L-alanyl)-α-D-glucopyranoside dihydrochloride
  参考文献：
  名称：

  SYNTHESIS OF AMINOACYL SUGAR DERIVATIVES AND THEIR TASTE CHARACTERISTICS. I. 2,3-DI- O-AMINOACYL DERIVATIVES OF ALKYL d-GLUCOPYRANOSIDES

  摘要：

  Aminoacyl derivatives of methyl alpha- and beta-D-glucopyranosides have been synthesized in order to ascertain the structural features required for the perception of a sweet taste. 2,3-Di-O-(L-aminoacyl) derivatives of methyl alpha-D-glucopyranoside showed a strong sweet taste (16-35x sucrose), which decreased or disappeared when either one of the two L-aminoacyl groups was absent or substituted by a D-aminoacyl group. In the case of 2,3-di-O-(L-alanyl) derivatives of methyl D-glucopyranoside, the a-anomer was very sweet (16-25x suc.) whereas the beta-anomer was not sweet. The structural prerequisite for sweetness in this group of compounds proved to be the presence Of L-aminoacyl groups at C-2 and C-3, and the alpha-configuration at C-1. Its a-isopropyl anomer showed the highest sweetness (64x suc.), hence the increased lipophilicity is also an important criterion.

  DOI：

  10.1081/car-120003744
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropyl 4,6-O-benzylidene-2,3-di-O-(N-tert-butoxycarbonyl-L-alanyl)-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF AMINOACYL SUGAR DERIVATIVES AND THEIR TASTE CHARACTERISTICS. I. 2,3-DI- O-AMINOACYL DERIVATIVES OF ALKYL d-GLUCOPYRANOSIDES

  摘要：

  Aminoacyl derivatives of methyl alpha- and beta-D-glucopyranosides have been synthesized in order to ascertain the structural features required for the perception of a sweet taste. 2,3-Di-O-(L-aminoacyl) derivatives of methyl alpha-D-glucopyranoside showed a strong sweet taste (16-35x sucrose), which decreased or disappeared when either one of the two L-aminoacyl groups was absent or substituted by a D-aminoacyl group. In the case of 2,3-di-O-(L-alanyl) derivatives of methyl D-glucopyranoside, the a-anomer was very sweet (16-25x suc.) whereas the beta-anomer was not sweet. The structural prerequisite for sweetness in this group of compounds proved to be the presence Of L-aminoacyl groups at C-2 and C-3, and the alpha-configuration at C-1. Its a-isopropyl anomer showed the highest sweetness (64x suc.), hence the increased lipophilicity is also an important criterion.

  DOI：

  10.1081/car-120003744