3,4,6-tri-O-acetyl-2-deoxy-2-iodohydrin | 287737-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-iodohydrin
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-glucopyranose；[(2R,3R,4S)-3,4-diacetyloxy-6-hydroxy-5-iodooxan-2-yl]methyl acetate
• CAS: 287737-94-4
• 化学式: C₁₂H₁₇IO₈
• 分子量: 416.167
• InChiKey: LSOHLAQAZDXUHX-GYOGACSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-iodohydrin 在 碘苯二乙酸 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以53%的产率得到2,3,5-tri-O-acetyl-1-deoxy-4-O-formyl-1-bromo-1-iodo-D-arabinitol
  参考文献：
  名称：

  碳水化合物异头烷氧基的断裂：手性1-卤-1-溴化合物的新合成

  摘要：

  在溴的存在下，衍生自易得的碳水化合物的1,2-卤代醇与（二乙酰氧基碘）苯（DIB）的反应是合成具有一个碳原子的1-deoxy-1-halo-1-bromo-alditols的温和方法。少于原来的碳水化合物。该反应通过中间端基异头烷氧基的β-片段化而进行。这些1-卤-1-溴多羟基化合物可能是有机合成中有价值的合成中间体。

  DOI：

  10.1016/s0040-4039(03)01399-6
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-iodohydrin
  参考文献：
  名称：

  碳水化合物端基烷氧基的断裂：手性1-卤代-1-碘化合物的新合成。

  摘要：

  在通过碳水化合物1，2-卤代醇的C1-C2自由基裂解获得的1-卤代-1-碘代化合物中，发现少一个碳原子。通过与（二乙酰氧基碘）苯和碘反应时形成的卤代醇的异头烷氧基自由基来实现这种断裂。（1）; X ＝ Cl，Br，I]。

  DOI：

  10.1002/1521-3773(20010618)40:12<2326::aid-anie2326>3.0.co;2-y

文献信息

• Fragmentation of Carbohydrate Anomeric Alkoxy Radicals: A New Synthesis of Chiral 1-Halo-1-iodo Alditols
  作者：Concepción C. González、Alan R. Kennedy、Elisa I. León、Concepción Riesco-Fagundo、Ernesto Suárez

  DOI：10.1002/chem.200305294

  日期：2003.12.5

  reaction was achieved by radical fragmentation of the C1bond;C2 bond, triggered by the initially formed anomeric alkoxy radical, and subsequent trapping of the C2-radical by iodine atoms. This methodology is compatible with the stability of the protective groups most frequently used in carbohydrate chemistry. The potential utility of these 1-halo-1-iodo alditols as chiral synthons was evaluated by

  D-葡萄糖，D-半乳糖，D-乳糖，L-鼠李糖，D-allo和L-的1,2-氟代醇，1,2-氯代醇，1,2-溴代醇和1,2-碘代醇的处理具有（二乙酰氧基碘）苯/碘体系的碳水化合物的阿拉伯糖，3-脱氧-D-葡萄糖和3,4-二脱氧-D-葡萄糖家族提供了1-氟-1-碘，1-氯-1-碘1 -bromo-1-iodo和1,1-diiodo alditols分别具有出色的收率。通过最初形成的异头烷氧基自由基引发的C1键; C2键的自由基断裂，以及随后的碘原子对C2自由基的捕获，可以实现该反应。该方法与碳水化合物化学中最常用的保护基的稳定性兼容。
• d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses
  作者：Izabela Fokt、Slawomir Szymanski、Stanislaw Skora、Marcin Cybulski、Timothy Madden、Waldemar Priebe

  DOI：10.1016/j.carres.2009.06.016

  日期：2009.8

  Modified D-glucose and D-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives Of D-glucose and D-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-D-glucal. (C) 2009 Elsevier Ltd. All rights reserved.
• Iodophosphoryloxylation of Carbon−Carbon Multibonds and Its Application to Glycals
  作者：Takahito Muraki、Masataka Yokoyama、Hideo Togo

  DOI：10.1021/jo000296r

  日期：2000.7.1

  Iodophosphoryloxylation of carbon-carbon multibonds was attempted. Alkynes and cyclohexene were converted to the corresponding 1,2-iodophosphoryloxylated compounds in moderate to good yields with a trivalent iodine compound/iodine system, while glucal gave mainly the corresponding iodohydrin compound in this system. However, 2-deoxy-2-iodoglycosyl diphenylphosphinates were obtained from the corresponding glycals with a diphenylphosphinic acid/iodine/potassium carbonate system in good yields. Moreover, triethylborane smoothly reduced 2-deoxy-2-iodoglycosyl diphenylphosphinates to 2-deoxyglycosyl diphenylphosphinates in a 1,4-cyclohexadiene solvent.