[(2S,3R,4S,5S)-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl] 4-oxopentanoate | 866476-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S)-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl] 4-oxopentanoate
• CAS: 866476-72-4
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: YFNGYFNXJPKGCG-LLLHUVSDSA-N

物化性质

• 沸点：
  505.2±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S)-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl] 4-oxopentanoate 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 benzyl 2-O-levulinyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4-O-acetyl-α-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
• 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 27.5h， 生成 [(2S,3R,4S,5S)-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl] 4-oxopentanoate
  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

文献信息

• Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue
  作者：Peng Wang、Chunxia Li、Jing Zang、Ni Song、Xiuli Zhang、Yingxia Li

  DOI：10.1016/j.carres.2005.06.024

  日期：2005.9

  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.