benzyl 2-O-levulinyl-4-O-acetyl-β-L-arabinopyranoside | 866476-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-levulinyl-4-O-acetyl-β-L-arabinopyranoside
• 英文别名: [(2S,3R,4S,5S)-5-acetyloxy-4-hydroxy-2-phenylmethoxyoxan-3-yl] 4-oxopentanoate
• CAS: 866476-73-5
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: DVERIBVANCSKPL-KANFNMMFSA-N

物化性质

• 沸点：
  531.9±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-levulinyl-4-O-acetyl-β-L-arabinopyranoside 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-3)[levulinoyl(-2)]Ara4Ac
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024
• 作为产物：
  描述：

  L-阿拉伯糖 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 benzyl 2-O-levulinyl-4-O-acetyl-β-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024