3,6-di-O-acetyl-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-1-trichloroacetimido-α-D-glucopyranose | 245738-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-acetyl-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-1-trichloroacetimido-α-D-glucopyranose
• 英文别名: TBDMS(-4)Glc2Br3Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4-acetyloxy-5-bromo-3-[tert-butyl(dimethyl)silyl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 245738-62-9
• 化学式: C₁₈H₂₉BrCl₃NO₇Si
• 分子量: 585.779
• InChiKey: OAUAHOVVSFCQIC-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-di-O-acetyl-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-1-trichloroacetimido-α-D-glucopyranose 、 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-O-(3,6-di-O-acetyl-2-bromo-4-O-(tert-butyldimethyl)silyl-2-deoxy-β-D-glucopyranosyl)-2-O-benzyl-4,6-O-benzylidene-α-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：

  、 三氯乙腈 在 sodium hydride 作用下， 以59%的产率得到3,6-di-O-acetyl-4-O-(tert-butyldimethyl)silyl-2-deoxy-2-bromo-1-trichloroacetimido-α-D-glucopyranose
  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