3,4-di-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose | 368452-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose
• CAS: 368452-03-3
• 化学式: C₂₃H₂₃IO₇
• 分子量: 538.336
• InChiKey: PTLNYCIHLRIRSW-YWNPBTLJSA-N

物化性质

• 沸点：
  575.7±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose 在 palladium on activated charcoal 六甲基磷酰三胺 、 sodium azide 、 氢气 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 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 、 咪唑 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 反应 8.5h， 生成 3,4-di-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose
  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

• 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.