methyl 4,6-O-benzylidene-2-O-(N-tert-butoxycarbonyl-D-alanyl)-α-D-glucopyranoside | 460354-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2-O-(N-tert-butoxycarbonyl-D-alanyl)-α-D-glucopyranoside
• CAS: 460354-46-5
• 化学式: C₂₂H₃₁NO₉
• 分子量: 453.489
• InChiKey: DIKPRJJUTNZSSB-LUKZYIRMSA-N

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-O-(N-tert-butoxycarbonyl-D-alanyl)-α-D-glucopyranoside 在 吡啶 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 methyl 2-O-(D-alanyl)-3-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：

  甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷 、 BOC-D-丙氨酸 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到methyl 4,6-O-benzylidene-2-O-(N-tert-butoxycarbonyl-D-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