4-O-allyl-1-O-benzyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-butanetriol | 428857-94-7

• 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-allyl-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-(1-phenylmethoxy-4-prop-2-enoxybutan-2-yl)oxyoxan-2-yl]methyl benzoate
• CAS: 428857-94-7
• 化学式: C₄₈H₄₆O₁₂
• 分子量: 814.886
• InChiKey: KPMWMFADFOVKHK-ABJKHCOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  60
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 、 Dowex 50WX-4 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 63.0h， 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-(2-Allyloxy-ethyl)-2,2-dibutyl-[1,3,2]dioxastannolane 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 cesium fluoride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 4-O-allyl-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

文献信息

• 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.