4-chlorophenyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside | 309758-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chlorophenyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-(4-chlorophenyl)sulfanyl-5-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 309758-89-2
• 化学式: C₆₈H₇₀ClF₃O₁₃S
• 分子量: 1219.81
• InChiKey: FEDSDFRMTNREAB-NAGQFIACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  86
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-chlorophenyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以97%的产率得到4-chlorophenyl (3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (1→4)-Linked 2-Deoxy-2-fluoroglucose Oligomers. 1

  摘要：

  [GRAPHICS]Thioglycosides of natural monosaccharides are readily converted into their corresponding chlorides by diphenylchlorosulfonium chloride. This reagent can likewise effect the conversion of the more stable 4-chlorophenylthio 2-deoxy-2-fluoroglucose derivatives into chloride glycosyl donors. On the basis of this activation strategy, it was possible to assemble unnatural oligosaccharides composed of 2-fluorodeoxy sugars.

  DOI：

  10.1021/ol006529i
• 作为产物：
  描述：

  4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl chloride 在 2,6-二叔丁基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 4-chlorophenyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (1→4)-Linked 2-Deoxy-2-fluoroglucose Oligomers. 1

  摘要：

  [GRAPHICS]Thioglycosides of natural monosaccharides are readily converted into their corresponding chlorides by diphenylchlorosulfonium chloride. This reagent can likewise effect the conversion of the more stable 4-chlorophenylthio 2-deoxy-2-fluoroglucose derivatives into chloride glycosyl donors. On the basis of this activation strategy, it was possible to assemble unnatural oligosaccharides composed of 2-fluorodeoxy sugars.

  DOI：

  10.1021/ol006529i