1-O-benzyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-butanetriol | 428857-87-8

• 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: 1-O-benzyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-butanetriol
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2S)-4-hydroxy-1-phenylmethoxybutan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 428857-87-8
• 化学式: C₄₅H₄₂O₁₂
• 分子量: 774.821
• InChiKey: JTDCCTFPJWWHDN-ZMTNCQJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 18.0h， 以90%的产率得到4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-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
• 作为产物：
  描述：

  (+/-)-4-O-allyl-1-O-benzyl-1,2,4-butanetriol 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 1-O-benzyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-butanetriol
  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