1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose | 358369-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
• 英文别名: (2R,3R,4S,5S,6R)-2-[(R)-fluoro-[(1R,2R,4R,5S,6R)-5-hydroxy-3,8,9-trioxatricyclo[4.2.1.02,4]nonan-4-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 358369-22-9
• 化学式: C₁₃H₁₉FO₉
• 分子量: 338.287
• InChiKey: WLZPACYPNCZUAQ-GGYMYEGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 15.0h， 以96%的产率得到4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1R)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462
• 作为产物：
  描述：

  isolevoglucosenone 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 二乙胺基三氟化硫 、 氨 、 sodium 、 二乙基碘化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462

文献信息

• Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-<i>C</i>-[(1<i>R</i>)-2,6-anhydro-1-deoxy-1-fluoro-<scp>d</scp>-<i>g</i><i>lycero</i>-<scp>d</scp>-<i>g</i><i>ulo</i>- heptitol-1-<i>C</i>-yl]-β-<scp>d</scp>-<i>g</i><i>ulo</i>-furanose:  First Example of a Monofluoromethylene-Linked <i>C</i>-Disaccharide
  作者：Jesús Jiménez-Barbero、Raynald Demange、Kurt Schenk、Pierre Vogel

  DOI：10.1021/jo0102462

  日期：2001.7.1

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.