(−)-(7S,9S)-7-(β-D-glucopyranosyloxy)-8,9-dihydrobenzofuran-2(4H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (−)-(7S,9S)-7-(β-D-glucopyranosyloxy)-8,9-dihydrobenzofuran-2(4H)-one
• 英文别名: (6S,7aS)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,7a-dihydro-6H-1-benzofuran-2-one
• 化学式: C₁₄H₁₈O₈
• 分子量: 314.292
• InChiKey: NTDAFPROCLCPBL-RJXIUGTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 吡啶 、 咪唑 、 potassium cyanide 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 碘 、 silver trifluoromethanesulfonate 、 mercury(II) trifluoroacetate 、 sodium hydride 、 溶剂黄146 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 (−)-(7S,9S)-7-(β-D-glucopyranosyloxy)-8,9-dihydrobenzofuran-2(4H)-one
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129

文献信息

• Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.
  作者：Kenji Mori、Gérard Audran、Yoshiaki Nakahara、Masahiko Bando、Masaru Kido

  DOI：10.1016/s0040-4039(96)02375-1

  日期：1997.1

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes
  作者：Yoshifumi Urakawa、Takanori Sugimoto、Hirotaka Sato、Minoru Ueda

  DOI：10.1016/j.tetlet.2004.05.129

  日期：2004.7

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.