3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside] | 1039374-29-2

• 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: 3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside]
• 英文别名: benzyl (2S,3S,4S,5R,6R)-4-[[(3aS,6S,7R,7aS)-7-[2-(azidomethyl)benzoyl]oxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3,5,6-tribenzoyloxyoxane-2-carboxylate
• CAS: 1039374-29-2
• 化学式: C₅₀H₄₅N₃O₁₅
• 分子量: 927.918
• InChiKey: JKOUVTXQTAZTEZ-SJFVLEBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  192
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside] 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到3,4-O-isopropylidene-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside]
  参考文献：
  名称：

  Synthesis of Betavulgaroside III, a Representative Triterpene seco-Glycoside

  摘要：

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.

  DOI：

  10.1021/jo800669h
• 作为产物：
  描述：

  phenyl 3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-1-thio-α-L-arabinopyranoside 、 benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到3,4-O-isopropylidene-2-O-(2-azidomethylbenzoyl)-α-L-arabinopyranosyl-(1->3)-[benzyl 1,2,4-tri-O-benzoyl-α-D-glucuronopyranoside]
  参考文献：
  名称：

  Synthesis of Betavulgaroside III, a Representative Triterpene seco-Glycoside

  摘要：

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.

  DOI：

  10.1021/jo800669h

文献信息

• Synthesis of Betavulgaroside III, a Representative Triterpene <i>seco</i>-Glycoside
  作者：Shilei Zhu、Yingxia Li、Biao Yu

  DOI：10.1021/jo800669h

  日期：2008.7.1

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.