[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-iodooxan-2-yl] acetate | 259169-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-iodooxan-2-yl] acetate
• CAS: 259169-89-6
• 化学式: C₈H₁₃IO₆
• 分子量: 332.092
• InChiKey: SQYRWTRRIXZBKL-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-iodooxan-2-yl] acetate 在 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Concerning the Origin of the High β-Selectivity of Glycosidation Reactions of 2-Deoxy-2-iodo-glucopyranosyl Trichloroacetimidates

  摘要：

  [GRAPHICS]Studies on the glycosidation reactions of conformationally constrained glycosyl imidates 8a and 8b were performed to evaluate the possible involvement of "conformationally inverted" oxonium ion intermediates in glycosidation reactions with 2-deoxy-2-iodo-glucopyranosyl donors. The mechanistic implications of this study are discussed, and intermediates 23 and 24 are invoked to rationalize the observed beta-selectivities.

  DOI：

  10.1021/ol027066e
• 作为产物：
  描述：

  2-deoxy-2-iodo-3,4,6-tri-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl acetate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-iodooxan-2-yl] acetate
  参考文献：
  名称：

  Concerning the Origin of the High β-Selectivity of Glycosidation Reactions of 2-Deoxy-2-iodo-glucopyranosyl Trichloroacetimidates

  摘要：

  [GRAPHICS]Studies on the glycosidation reactions of conformationally constrained glycosyl imidates 8a and 8b were performed to evaluate the possible involvement of "conformationally inverted" oxonium ion intermediates in glycosidation reactions with 2-deoxy-2-iodo-glucopyranosyl donors. The mechanistic implications of this study are discussed, and intermediates 23 and 24 are invoked to rationalize the observed beta-selectivities.

  DOI：

  10.1021/ol027066e

文献信息

• Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals
  作者：Andreas Kirschning、Martin Jesberger、Holger Monenschein

  DOI：10.1016/s0040-4039(99)01925-5

  日期：1999.12

  Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent

  制备了聚合物支撑的亲电子试剂，其在非常温和的条件下可有效地添加至碳水化合物衍生的糖基中。取决于最初用于氧化与聚合物结合的卤化物1a或1b的高价试剂，可以进行乙酰氧基卤化或叠氮碘化。用糖衍生的缩醛，可以极好的收率产生2-脱氧-2-卤代吡喃糖基乙酸酯或叠氮化物。游离羟基是可容忍的。甚至完全未保护的葡糖醛23也可用于2-脱氧-2-碘代乙酸糖基乙酸酯24a，b的短合成。
• Procurement of 2-deoxy-2-iodo-d-glucose (2-DIG)
  作者：Christophe Morin

  DOI：10.1016/j.tetlet.2006.05.091

  日期：2006.7

  The heretofore elusive 2-deoxy-2-iodo-D-glucose (2-DIG), the iodinated analogue of FDG (2-fluoro-2-deoxy-D-glucose)-a PET imaging agent of glucose cellular uptake-can be obtained from D-glucal and is a stable compound. (c) 2006 Elsevier Ltd. All rights reserved.