6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-1-trichloroacetimido-α-D-glucopyranose | 245738-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-1-trichloroacetimido-α-D-glucopyranose
• 英文别名: TBDMS(-3)[pivaloyl(-4)]Glc2I6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-2-(acetyloxymethyl)-4-[tert-butyl(dimethyl)silyl]oxy-5-iodo-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 2,2-dimethylpropanoate
• CAS: 245738-44-7
• 化学式: C₂₁H₃₅Cl₃INO₇Si
• 分子量: 674.86
• InChiKey: JZXAVRKKQMRITB-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷 、 6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-1-trichloroacetimido-α-D-glucopyranose 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 6-O-(6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 、 methyl 6-O-(6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-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：

  在 2,6-二甲基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-O-acetyl-3-O-(tert-butyldimethyl)silyl-2-deoxy-2-iodo-4-O-pivaloyl-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