1:6-anhydro-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-D-glucopyranoside | 245738-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1:6-anhydro-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-D-glucopyranoside
• CAS: 245738-60-7
• 化学式: C₁₂H₂₃BrO₄Si
• 分子量: 339.302
• InChiKey: REXCFRCWOKCQLY-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1:6-anhydro-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-D-glucopyranoside 、 乙酸酐 在 三氟乙酸 作用下， 反应 2.0h， 生成 acetyl 3,6-di-O-acetyl-2-deoxy-2-bromo-4-O-t-butyldimethyl-D-glucopyranoside 、 acetyl 3,6-di-O-acetyl-2-deoxy-2-bromo-4-O-t-butyldimethyl-D-glucopyranoside
  参考文献：
  名称：

  2-Deoxy-2-iodo- and 2-Deoxy-2-bromo-α-glucopyranosyl Trichloroacetimidates:  Highly Reactive and Stereoselective Donors for the Synthesis of 2-Deoxy-β-glycosides

  摘要：

  [GRAPHICS]5-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2 deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl accepters using TBS-OTf as the activating agent. beta-Glycosides are obtained with greater than or equal to 19:1 selectivity in six of the seven examples reported herein.

  DOI：

  10.1021/ol9908070
• 作为产物：
  描述：

  D-葡萄烯糖 在 咪唑 、 3 A molecular sieve 、 三丁基氧化锡 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.5h， 生成 1:6-anhydro-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-D-glucopyranoside
  参考文献：
  名称：

  2-Deoxy-2-iodo- and 2-Deoxy-2-bromo-α-glucopyranosyl Trichloroacetimidates:  Highly Reactive and Stereoselective Donors for the Synthesis of 2-Deoxy-β-glycosides

  摘要：

  [GRAPHICS]5-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2 deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl accepters using TBS-OTf as the activating agent. beta-Glycosides are obtained with greater than or equal to 19:1 selectivity in six of the seven examples reported herein.

  DOI：

  10.1021/ol9908070