4-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside | 309758-81-4

• 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: 4-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-6-(4-chlorophenyl)sulfanyl-5-fluoro-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 309758-81-4
• 化学式: C₂₆H₂₆ClFO₄S
• 分子量: 489.007
• InChiKey: OYAHUHNQSSYDCH-SDVOOXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 2,6-二叔丁基吡啶 、 silver trifluoromethanesulfonate 、 chlorodiphenylsulfonium chloride 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 (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-α-D-glucopyranosyl chloride
  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-chlorophenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-1-thio-β-D-glucopyranoside 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到4-chlorophenyl 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

文献信息

• Synthesis of (1→4)-Linked 2-Deoxy-2-fluoroglucose Oligomers. 1
  作者：Shin Sugiyama、Wasim Haque、James Diakur

  DOI：10.1021/ol006529i

  日期：2000.11.1

  [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.