phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 354152-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6R)-3-acetyloxy-6-[(1,3-dioxoisoindol-2-yl)methoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 354152-80-0
• 化学式: C₁₉H₁₉NO₈
• 分子量: 389.362
• InChiKey: ROQJQHMRJVOZPA-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 甲醇 、 水 、 三乙胺 作用下， 反应 5.0h， 以86%的产率得到phthalimidomethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  N-邻苯二甲酰亚胺甲基四-O-酰基-α-d-甘露吡喃糖苷的合成及降血脂活性

  摘要：

  摘要一种易于合成的异源纯邻苯二甲酰亚甲基2,3,4,6-四-O-乙酰基和邻苯二甲酰亚胺2,3-二-O-乙酰基-4,6-二-O-苯甲酰基-α-d-甘露吡喃糖苷（描述了从N-羟甲基邻苯二甲酰亚胺和三-O-乙酰基-d-葡糖醛开始的图6和9b）。已经测试了化合物3、6、8、9a和9b在小鼠中的降血脂活性。所有这些化合物均显示血浆胆固醇和甘油三酯水平显着降低。已经发现化合物9b具有最高的活性。

  DOI：

  10.1016/s0008-6215(01)00088-x
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 、 乙酰化葡萄烯糖 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 1.25h， 以76.3%的产率得到phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  N-邻苯二甲酰亚胺甲基四-O-酰基-α-d-甘露吡喃糖苷的合成及降血脂活性

  摘要：

  摘要一种易于合成的异源纯邻苯二甲酰亚甲基2,3,4,6-四-O-乙酰基和邻苯二甲酰亚胺2,3-二-O-乙酰基-4,6-二-O-苯甲酰基-α-d-甘露吡喃糖苷（描述了从N-羟甲基邻苯二甲酰亚胺和三-O-乙酰基-d-葡糖醛开始的图6和9b）。已经测试了化合物3、6、8、9a和9b在小鼠中的降血脂活性。所有这些化合物均显示血浆胆固醇和甘油三酯水平显着降低。已经发现化合物9b具有最高的活性。

  DOI：

  10.1016/s0008-6215(01)00088-x

文献信息

• Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-d-mannopyranosides
  作者：Rajendra M Srivastava、Fernando J.S Oliveira、Ladjane P da Silva、João R de Freitas Filho、Shalom P Oliveira、Vera L.M Lima

  DOI：10.1016/s0008-6215(01)00088-x

  日期：2001.6

  Abstract A facile synthesis of anomerically pure phthalimidomethyl 2,3,4,6-tetra- O -acetyl- and phthalimidomethyl 2,3-di- O -acetyl-4,6-di- O -benzoyl-α- d -mannopyranosides ( 6 and 9b ) starting from N -hydroxymethylphthalimide and tri- O -acetyl- d -glucal is described. Compounds 3 , 6 , 8 , 9a and 9b have been tested for their hypolipidemic activity in mice. All these compound showed significant

  摘要一种易于合成的异源纯邻苯二甲酰亚甲基2,3,4,6-四-O-乙酰基和邻苯二甲酰亚胺2,3-二-O-乙酰基-4,6-二-O-苯甲酰基-α-d-甘露吡喃糖苷（描述了从N-羟甲基邻苯二甲酰亚胺和三-O-乙酰基-d-葡糖醛开始的图6和9b）。已经测试了化合物3、6、8、9a和9b在小鼠中的降血脂活性。所有这些化合物均显示血浆胆固醇和甘油三酯水平显着降低。已经发现化合物9b具有最高的活性。
• Exclusive Formation of a-Anomers in NbCl5-Promoted Ferrier Rearrangement for the Synthesis of 2,3-Unsaturated Glycosides
  作者：Rajendra M. Srivastava、Ronaldo N. de Oliveira、Adriana C. N. de Melo、Denis Sinou

  DOI：10.3987/com-06-10812

  日期：——
• Microwave-induced synthesis of 2,3-unsaturated O-glycosides under solvent-free conditions
  作者：Ronaldo N. de Oliveira、João R.de Freitas Filho、Rajendra M. Srivastava

  DOI：10.1016/s0040-4039(02)00156-9

  日期：2002.3

  Microwave irradiation of it mixture of tri-O-acetyl-D-glucal 1 and an appropriate alcohol 2a f. in the presence of Montmorillonite K-10 as a catalyst, provided unsaturated glycosides 3a-f in much shorter time and in yields comparable with conventional heating. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides
  作者：Xiang-Bao Meng、Dong Han、Su-Na Zhang、Wei Guo、Jing-Rong Cui、Zhong-Jun Li

  DOI：10.1016/j.carres.2007.03.009

  日期：2007.7

  3,4,6-Tri-O-acetyl-D -gal actal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',46'-hexa-0-acetyl-D-lactaI were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS). (C) 2007 Elsevier Ltd. All rights reserved.