2,3,4-tri-O-benzoyl-6-O-methyl-β-D-glucopyranosyl fluoride | 1159181-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-6-O-methyl-β-D-glucopyranosyl fluoride
• 英文别名: 2,3,4-tri-O-benzoyl-1-deoxy-1-fluoro-6-methyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-fluoro-2-(methoxymethyl)oxan-3-yl] benzoate
• CAS: 1159181-10-8
• 化学式: C₂₈H₂₅FO₈
• 分子量: 508.5
• InChiKey: QTIBZPBNAPBFAY-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-trityl-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-benzoyl-6-O-methyl-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides

  摘要：

  Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.

  DOI：

  10.1080/07328303.2010.540055

文献信息

• DAST-Mediated Regioselective Anomeric Group Migration in Saccharides
  作者：Po-Chiao Lin、Avijit Kumar Adak、Shau-Hua Ueng、Li-De Huang、Kuo-Ting Huang、Ja-an Annie Ho、Chun-Cheng Lin

  DOI：10.1021/jo900516r

  日期：2009.6.5

  When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.
• Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides
  作者：Aslan M. Esmurziev、Nebojsa Simic、Bård Helge Hoff、Eirik Sundby

  DOI：10.1080/07328303.2010.540055

  日期：2010.9

  Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.