1,2-O-isopropylidene-3,4-di-O-benzoyl-β-D-fructopyranose | 99648-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3,4-di-O-benzoyl-β-D-fructopyranose
• 英文别名: 3,4-di-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose；[(5S,6S,7R,8R)-6-benzoyloxy-8-hydroxy-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decan-7-yl] benzoate
• CAS: 99648-59-6
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: CPMWKENCUXUOIT-GBPOLFSSSA-N

物化性质

• 沸点：
  581.9±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,4-di-O-benzoyl-β-D-fructopyranose 在 palladium on activated charcoal 咪唑 、 六甲基磷酰三胺 、 sodium azide 、 氢气 、 碘 、 sodium methylate 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 70.0~80.0 ℃ 、400.0 kPa 条件下， 反应 24.0h， 生成 Alpha-葡萄糖苷酶
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221
• 作为产物：
  描述：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 8.5h， 生成 1,2-O-isopropylidene-3,4-di-O-benzoyl-β-D-fructopyranose
  参考文献：
  名称：

  Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

  摘要：

  Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp(2)-hybridized endocyclic ring nitrogen.

  DOI：

  10.1021/jo0499221

文献信息

• Synthesis of Anomeric Sulfimides and Their Use as a New Family of Glycosyl Donors
  作者：Florence Chéry、Stéphanie Cassel、Hans Peter Wessel、Patrick Rollin

  DOI：10.1002/1099-0690(20021)2002:1<171::aid-ejoc171>3.0.co;2-7

  日期：2002.1

  We introduce a convenient synthesis of anomeric sulfimides, the ability of which to act as glycosyl donors has been tested with various thiophilic reagents and acceptors.

  我们介绍了一种方便的异头磺酰亚胺合成方法，其作为糖基供体的能力已经用各种亲硫试剂和受体进行了测试。
• Neue synthese und kristallstruktur der leucrose
  作者：Joachim Thiem、Matthias Kleeberg、Karl-Heinz Klaska

  DOI：10.1016/0008-6215(89)84086-8

  日期：1989.6

  Abstract Boron trifluoride-catalyzed condensation of 2,3,4,6-tetra- O -benzyl-α- d -glucopyranosyl fluoride ( 2 ) with 3,4-di- O -benzoyl-1,2- O -isopropylidene-β- d -fructopyranose ( 1 ) gave preferentially the α- d -(1→5)-linked disaccharide 8 . Similarly, glycosylation of benzyl 1,3,4-tri- O -benzoyl-β- d -fructopyranoside ( 4 ) with 2 gave preponderantly a disaccharide derivative that, after cleavage

  摘要三氟化硼催化2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖基氟（2）与3,4-二-O-苯甲酰基-1,2-O-异亚丙基-β的缩合反应-d-果糖吡喃糖（1）优先给出α-d-（1→5）-连接的二糖8。类似地，将苄基1,3,4-三-O-苯甲酰基-β-d-果糖吡喃糖苷（4）糖基化，主要得到二糖衍生物，该二糖衍生物在苯甲酰基和苄基均被裂解后可提供白糖（5-O -α-d-吡喃葡萄糖基-β-d-果糖吡喃糖； 13）。这在正交晶空间群P 2 1 2 1 2 1中结晶，该晶群在单位位置的两个单元中以4：1的比例包含四个糖和四个水分子。如预期的那样，果糖吡喃糖和吡喃葡萄糖环均分别采用2 C 5（d）或4 C 1（d）椅子构象。
• Lichtenthaler, Frieder W.; Doleschal, Walter; Hahn, Susanne, Liebigs Annalen der Chemie, 1985, # 12, p. 2454 - 2464
  作者：Lichtenthaler, Frieder W.、Doleschal, Walter、Hahn, Susanne

  DOI：——

  日期：——
• Synthesis and evaluation of fructose analogues as inhibitors of the d -fructose transporter GLUT5
  作者：Arnaud Tatibouët、Jing Yang、Christophe Morin、Geoffrey D. Holman

  DOI：10.1016/s0968-0896(00)00108-5

  日期：2000.7

  We have examined the specificity and binding-site spatial requirements of the fructose transporter GLUT5. Interaction with a series of fructofuranosides and fructopyranosides suggests that both furanose and pyranose ring forms of D-fructose combine with GLUT5. The epimers of D-fructose all have low affinity for GLUT5 suggesting that the transporter requires all hydroxyls to be in the fructo-configuration. Similarly there is poor tolerance of all allyl derivatives of D-fructose except 6-O-allyl-D-fructo-furanose. Therefore, the C-6 position offers the most suitable position for development of affinity probes and labels for exploring GLUT5 biochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.
• d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5
  作者：Arnaud Tatibouët、Myriam Lefoix、Jonathan Nadolny、Olivier R Martin、Patrick Rollin、Jing Yang、Geoffrey D Holman

  DOI：10.1016/s0008-6215(01)00153-7

  日期：2001.7

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.