laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside | 484002-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside
• 英文别名: [(3S,4S,5R,6R)-4,5-dibenzoyloxy-6-[[(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-3-hydroxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S)-5',7,9,13-tetramethyl-19-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-2-yl]methoxy]oxan-3-yl] benzoate
• CAS: 484002-10-0
• 化学式: C₇₃H₈₀O₁₈
• 分子量: 1245.43
• InChiKey: UBYHNUXKOIJELH-BHHUAQOFSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  91
• 可旋转键数：
  20
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  224
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-β-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 、 laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到[(3S,4S,5R,6R)-4,5-dibenzoyloxy-6-[[(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S)-5',7,9,13-tetramethyl-19-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-tribenzoyloxyoxan-2-yl]oxyoxan-2-yl]methoxy]oxan-3-yl] benzoate
  参考文献：
  名称：

  Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I

  摘要：

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

  DOI：

  10.1021/jo026103c
• 作为产物：
  描述：

  薯蓣皂素 在 palladium on activated charcoal 吡啶 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 氢气 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 38.5h， 生成 laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I

  摘要：

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

  DOI：

  10.1021/jo026103c