2-O-levulinyl-3-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-4-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate | 866476-79-1

• 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: 2-O-levulinyl-3-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-4-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Ara(a1-3)[levulinoyl(-2)]Ara4Ac(b)-O-C(NH)CCl3；[(3S,4S,5R,6S)-6-[(2R,3R,4S,5S)-5-acetyloxy-3-(4-oxopentanoyloxy)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxy-4,5-dibenzoyloxyoxan-3-yl] benzoate
• CAS: 866476-79-1
• 化学式: C₄₀H₃₈Cl₃NO₁₅
• 分子量: 879.098
• InChiKey: SJRAIFNHGIIFSN-UJIJRDPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  209
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-O-levulinyl-3-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-4-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到3-O-[2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1->3)-2-O-levulinyl-4-O-acetyl-α-L-arabinopyranosyl]ursolic acid-28-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl] ester
  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 palladium on activated charcoal 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 2-O-levulinyl-3-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-4-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate
  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