(22S)-5α-cholestane-1β,3β,16β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside | 142182-46-5

• 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: (22S)-5α-cholestane-1β,3β,16β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside
• 英文别名: (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside；(22S)-16β-[(β-D-glucopyranosyl)oxy]-3β,22-dihydroxy-5α-cholestan-1β-yl α-L-rhamnopyranoside；(2R,3R,4R,5R,6S)-2-[[(1R,3R,5S,8S,9S,10S,13S,14S,16S,17R)-3-hydroxy-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-16-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl]oxy]-6-methyloxane-3,4,5-triol
• CAS: 142182-46-5
• 化学式: C₃₉H₆₈O₁₃
• 分子量: 744.961
• InChiKey: XWYZBVLUVOCIOL-PQKRKDDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (22S)-5α-cholestane-1β,3β,16β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside 在 dioxane HCl 作用下， 反应 1.0h， 以25.0 mg的产率得到aglycon
  参考文献：
  名称：

  来自 Ornithogalum thyrsoides 球茎的新胆甾烷 Bisdesmosides

  摘要：

  已从 Ornithogalum thyrsoides 的新鲜鳞茎中分离出四种新的胆甾烷 bisdesmosides。它们的结构通过光谱分析和化学证据确定为 (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside (1) , (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-(6-O-acetyl-β-D-glupyranoside) (2), (22S )-5α-cholest-24-ene-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glupyranoside (3), 和 (22S)-5α-cholest- 24-ene-1β

  DOI：

  10.1246/bcsj.65.1120
• 作为产物：
  描述：

  (22S)-5α-cholest-24-ene-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以5 mg的产率得到(22S)-5α-cholestane-1β,3β,16β,22-tetraol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside
  参考文献：
  名称：

  来自 Ornithogalum thyrsoides 球茎的新胆甾烷 Bisdesmosides

  摘要：

  已从 Ornithogalum thyrsoides 的新鲜鳞茎中分离出四种新的胆甾烷 bisdesmosides。它们的结构通过光谱分析和化学证据确定为 (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside (1) , (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-(6-O-acetyl-β-D-glupyranoside) (2), (22S )-5α-cholest-24-ene-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glupyranoside (3), 和 (22S)-5α-cholest- 24-ene-1β

  DOI：

  10.1246/bcsj.65.1120

文献信息

• Steroidal glycosides from Allium albopilosum and A. ostrowskianum
  作者：Yoshihiro Mimaki、Kazuhiro Kawashima、Toshihiro Kanmoto、Yutaka Sashida

  DOI：10.1016/0031-9422(93)85362-u

  日期：1993.10

  Chemical studies of the bulbs of Allium albopilosum and A. ostrowskianum have led to the isolation of two new steroidal saponins and four new cholestane glycosides together with several known compounds. The structures of the new compounds were established by the spectroscopic data, hydrolysis and chemical correlations as (25 R and S)-5alpha-spirostane-2alpha,3beta,6beta-triol 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-[3-O-acetyl-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2-O-[(S)-3-hydroxy-3-methylglutaroyl]-5alpha-spirostane-2alpha,3beta,6beta-triol 3-O-O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-Xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-d-galactopyranoside}, (22S)-cholest-5-ene-1beta,3beta,16beta,22-tetraol 1-O-alpha-L-rhamnopyranoside 16-O-O-alpha-L-rhamnopyr-anosyl-(1-->3)-beta-D-glucopyranoside), 1beta,3beta,16beta-trihydroxycholest-5-en-22-one 1-O-alpha-L-rhamnopyranoside 16-O-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside}, 1beta,3beta,16beta-trihydroxy-5alpha-cholestan-22-one 1-O-alpha-L-rhamnopyranoside 16-O-O-alpha-L-rhamnopyranosYl-(1-->3)-beta-D-glucopyranoside} and (22S)-cholest-5-ene-1beta,3beta,16beta,22-tetraol 16-O-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside}.