3-O-(β-D-glucopyranosyl)-(3S)-3,4-dihydroxy-butanoic acid | 288852-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-O-(β-D-glucopyranosyl)-(3S)-3,4-dihydroxy-butanoic acid
• 英文别名: 3-(S)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid；goodyeroside B；(3s)-3-(beta-d-Glucopyranosyloxy)-4-hydroxybutanoic acid；(3S)-4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanoic acid
• CAS: 288852-23-3
• 化学式: C₁₀H₁₈O₉
• 分子量: 282.248
• InChiKey: XBHPIDRJPMHODV-MBOSOLAWSA-N

物化性质

• 沸点：
  636.4±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-(β-D-glucopyranosyl)-(3S)-3,4-dihydroxy-butanoic acid 在 硫酸 水 作用下， 生成 goodyeroside A
  参考文献：
  名称：

  Hepatoprotective Aliphatic Glycosides from Three Goodyera Species.

  摘要：

  保肝脂肪族糖苷 3-(S)-3-β-D-吡喃葡萄糖氧基丁内酯 (1) 及其同源物 3-(S)-3-β-D-吡喃葡萄糖氧基-4-羟基丁酸 (2) 作为主要成分从三个 Goodyera 物种 G. schlechtendaliana REICHB 的全株。 fil.，G. matsumurana SCHLTR。 G. KER-GAWL 变色。 1和2的结构已通过NMR、MS光谱和化学手段确定。在纯化步骤中，以CHCl3-MeOH-H2O为溶剂，通过硅胶催化，内酯环裂解，化合物1转化为其甲酯形式(5)。另一方面，在没有MeOH的情况下通过相同的纯化程序以高产率获得1。基于这一事实，确定了一种简单且经济的纯化1的方法。发现化合物1和2对原代培养的大鼠肝细胞由四氯化碳引起的肝损伤具有保肝作用。

  DOI：

  10.1248/bpb.23.731
• 作为产物：
  描述：

  1-O-benzyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-butanetriol 在 ruthenium trichloride 、 sodium periodate 、 sodium methylate 作用下， 以 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 21.0h， 生成 3-O-(β-D-glucopyranosyl)-(3S)-3,4-dihydroxy-butanoic acid
  参考文献：
  名称：

  Synthesis of 3‐O‐β‐D‐Glucopyranosyl‐(3R)‐hydroxybutanolide (Kinsenoside) and 3‐O‐β‐D‐Glucopyranosyl‐(3S)‐hydroxybutanolide (Goodyeroside A)

  摘要：

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.

  DOI：

  10.1081/car-200050541

文献信息

• Hepatoprotective Aliphatic Glycosides from Three Goodyera Species.
  作者：Xiao-Ming DU、Ning-Yi SUN、Yang CHEN、Nobuto IRINO、Yukihiro SHOYAMA

  DOI：10.1248/bpb.23.731

  日期：——

  Hepatoprotective aliphatic glycosides 3-(S)-3-β-D-glucopyranosyloxybutanolide (1) and its congener, 3-(S)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid (2) were isolated as major constituents from the whole plants of three Goodyera species, G. schlechtendaliana REICHB. fil., G. matsumurana SCHLTR. and G. discolor KER-GAWL. The structures of 1 and 2 have been determined by NMR, MS spectroscopic and chemical means. Compound 1 was converted into its methyl ester form (5) during the purification step, when the lactone ring was cleaved by catalysis of silica gel with the CHCl3-MeOH-H2O as a solvent. On the other hand, 1 was obtained in a high yield by the same purification procedure without MeOH. Based on this fact, a simple and economic method for the purification of 1 was confirmed. Compounds 1 and 2 were found to have a hepatoprotective effect on liver injury induced by carbon tetrachloride in primary cultured rat hepatocytes.

  保肝脂肪族糖苷 3-(S)-3-β-D-吡喃葡萄糖氧基丁内酯 (1) 及其同源物 3-(S)-3-β-D-吡喃葡萄糖氧基-4-羟基丁酸 (2) 作为主要成分从三个 Goodyera 物种 G. schlechtendaliana REICHB 的全株。 fil.，G. matsumurana SCHLTR。 G. KER-GAWL 变色。 1和2的结构已通过NMR、MS光谱和化学手段确定。在纯化步骤中，以CHCl3-MeOH-H2O为溶剂，通过硅胶催化，内酯环裂解，化合物1转化为其甲酯形式(5)。另一方面，在没有MeOH的情况下通过相同的纯化程序以高产率获得1。基于这一事实，确定了一种简单且经济的纯化1的方法。发现化合物1和2对原代培养的大鼠肝细胞由四氯化碳引起的肝损伤具有保肝作用。
• Synthesis of 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>R</i>)‐hydroxybutanolide (Kinsenoside) and 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>S</i>)‐hydroxybutanolide (Goodyeroside A)
  作者：Katsuhiko Suzuki、Nobuyuki Suzuki、Masanori Yamaura、Toyokichi Yoshizawa

  DOI：10.1081/car-200050541

  日期：2005.1

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.