4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(3R)-3,4-dihydroxy-butanoic acid | 850893-26-4

• 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: 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(3R)-3,4-dihydroxy-butanoic acid
• 英文别名: (3R)-4-benzoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxybutanoic acid
• CAS: 850893-26-4
• 化学式: C₄₅H₃₈O₁₄
• 分子量: 802.788
• InChiKey: PKGMKMCCHJDXBL-SAMAVBSDSA-N

物化性质

• 沸点：
  899.6±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  59
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  187
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(3R)-3,4-dihydroxy-butanoic acid 在 Dowex 50WX-4 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 生成 金线莲苷
  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
• 作为产物：
  描述：

  4-O-allyl-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 acetate 、 溶剂黄146 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 42.0h， 生成 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(3R)-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