3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 709030-17-1

• 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: 3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3-acetyloxy-5-iodophenoxy)oxan-2-yl]methyl acetate
• CAS: 709030-17-1
• 化学式: C₂₂H₂₅IO₁₂
• 分子量: 608.338
• InChiKey: XDJWDSLOEPPLAA-QMCAAQAGSA-N

物化性质

• 沸点：
  607.8±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 palladium diacetate 、 三正丁胺 、 苄基三乙基氯化铵 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 虎杖甙
  参考文献：
  名称：

  A Novel, Convenient Synthesis of the 3‐O‐β‐D‐ and 4′‐O‐β‐D‐Glucopyranosides of trans‐Resveratrol

  摘要：

  trans-Resveratrol-3-O-beta-D-glueupyranoside (trans-piceid, 2) and trans-resveratrol-4'-O-beta-D-glucupyranoside (trans-resveratroloside 3) are the naturally occurring O-glucoside conjugates of the polyphenolic stilbenoid trans-resveratrol 1. Recently, attention has been drawn towards the interesting biological properties of the glucoside conjugates 2 and 3 as well as those of the aglycone 1. The fact that only limited quantities can be obtained by extraction from natural sources has prompted the development of novel syntheses of 2 and 3, based on a convergent Heck-coupling strategy, which now conveniently allows for the preparation of multimilligram to gram quantities of each.

  DOI：

  10.1081/scc-120030744
• 作为产物：
  描述：

  5-碘邻苯二酚 在 吡啶 、 4-二甲氨基吡啶 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成 3-acetoxy-5-iodophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  A Novel, Convenient Synthesis of the 3‐O‐β‐D‐ and 4′‐O‐β‐D‐Glucopyranosides of trans‐Resveratrol

  摘要：

  trans-Resveratrol-3-O-beta-D-glueupyranoside (trans-piceid, 2) and trans-resveratrol-4'-O-beta-D-glucupyranoside (trans-resveratroloside 3) are the naturally occurring O-glucoside conjugates of the polyphenolic stilbenoid trans-resveratrol 1. Recently, attention has been drawn towards the interesting biological properties of the glucoside conjugates 2 and 3 as well as those of the aglycone 1. The fact that only limited quantities can be obtained by extraction from natural sources has prompted the development of novel syntheses of 2 and 3, based on a convergent Heck-coupling strategy, which now conveniently allows for the preparation of multimilligram to gram quantities of each.

  DOI：

  10.1081/scc-120030744

文献信息

• Synthetic Communications 2004, 34, 1565-1575
  作者：

  DOI：——

  日期：——