(3R,6S)-3-(4'-benzyloxy-(2'Z)-butenyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione | 176966-49-7

• 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: (3R,6S)-3-(4'-benzyloxy-(2'Z)-butenyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione
• 英文别名: (3R,6S)-6-methyl-4-[(1S)-1-phenylethyl]-3-[(Z)-4-phenylmethoxybut-2-enyl]morpholine-2,5-dione
• CAS: 176966-49-7
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: HQBSJEQGHKLGOH-XFQYFZAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,6S)-3-(4'-benzyloxy-(2'Z)-butenyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 在 3-氯苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-benzyloxymethyl-oxiranylmethyl)-6-methyl-4-(1-phenyl-ethyl)-morpholine-2,5-dione
  参考文献：
  名称：

  Synthesis of new chiral 1,4-morpholin-2,5-dione derivatives and evaluation as α-glucosidase inhibitors. Part 3

  摘要：

  A series of chiral 1,4-morpholin-2,5-dione derivatives were synthesized starting from chiral synthons 1 and 2, monolactim ethers derived from L- valine, and the absolute configurations of the new stereocentres were assigned. The substrates investigated behave as noncompetitive inhibitors against alpha-glucosidases and Eire inactive towards beta-glucosidase, alpha-mannosidase and alpha-galactosidase. Three of these substrates show very good and specific inhibition abilities towards alpha-glucosidase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.02.013
• 作为产物：
  描述：

  (Z)-4-(phenylmethoxy)-2-butenyl methanesulfonate 、 (6S,1'S)-6-methyl-4-(1'-phenylethyl)-1,4-morpholine-2,5-dione 在 lithium hexamethyldisilazane 作用下， 生成 (3R,6S)-3-(4'-benzyloxy-(2'Z)-butenyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione
  参考文献：
  名称：

  Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

  摘要：

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00079-1

文献信息

• Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine
  作者：Alessandra Madau、Gianni Porzi、Sergio Sandri

  DOI：10.1016/0957-4166(96)00079-1

  日期：1996.3

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd
• An improved procedure for the enantioselective synthesis of (+)- and (−)-cis-4-hydroxyprolines and bulgecinines
  作者：Lucia Graziani、Gianni Porzi、Sergio Sandri

  DOI：10.1016/0957-4166(96)00150-4

  日期：1996.5

  An efficient enantioselective synthesis of both the enantiomers of cis-4-hydroxy-proline and bulgecinine was accomplished starting from synthons 1 or 1'. The improved synthetic route to the aforesaid enantiomerically pure proline derivatives was established via a stereocontrolled double iodocyclization of 3(a,b) or 3'(a,b) Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of new chiral 1,4-morpholin-2,5-dione derivatives and evaluation as α-glucosidase inhibitors. Part 3
  作者：Antonio Arcelli、Daniele Balducci、Sonia de Fatima Estevao Neto、Gianni Porzi、Monica Sandri

  DOI：10.1016/j.tetasy.2007.02.013

  日期：2007.3

  A series of chiral 1,4-morpholin-2,5-dione derivatives were synthesized starting from chiral synthons 1 and 2, monolactim ethers derived from L- valine, and the absolute configurations of the new stereocentres were assigned. The substrates investigated behave as noncompetitive inhibitors against alpha-glucosidases and Eire inactive towards beta-glucosidase, alpha-mannosidase and alpha-galactosidase. Three of these substrates show very good and specific inhibition abilities towards alpha-glucosidase. (c) 2007 Elsevier Ltd. All rights reserved.