[(2S,3S,4R,5R,6S)-6-acetyloxy-4-hydroxy-5-iodo-2,4-dimethyloxan-3-yl] 2-methylpropanoate | 142841-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R,5R,6S)-6-acetyloxy-4-hydroxy-5-iodo-2,4-dimethyloxan-3-yl] 2-methylpropanoate
• CAS: 142841-34-7
• 化学式: C₁₃H₂₁IO₆
• 分子量: 400.211
• InChiKey: VCGORULLWZARCA-OERCDCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,5R,6S)-6-acetyloxy-4-hydroxy-5-iodo-2,4-dimethyloxan-3-yl] 2-methylpropanoate 在 Raney-Ni W-2 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of C-D-E trisaccharide precursors of olivomycin A.

  摘要：

  Syntheses of functionalized C-D-E trisaccharide precursors (16, 5) of olivomycin A are reported. A stereoselective C-D beta-glycosidation was accomplished by employing 2-deoxy-2-(phenylthio)-alpha-glucotrichloro-acetimidate 8. The alpha-D-E glycosidic linkage was introduced by using 2-deoxy-2-iodo-alpha-glycosyl acetate donor 14 as the glycosyl transfer agent.

  DOI：

  10.1021/jo00044a010
• 作为产物：
  描述：

  L-olivomycal 在 吡啶 、 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3S,4R,5R,6S)-6-acetyloxy-4-hydroxy-5-iodo-2,4-dimethyloxan-3-yl] 2-methylpropanoate
  参考文献：
  名称：

  Synthesis of C-D-E trisaccharide precursors of olivomycin A.

  摘要：

  Syntheses of functionalized C-D-E trisaccharide precursors (16, 5) of olivomycin A are reported. A stereoselective C-D beta-glycosidation was accomplished by employing 2-deoxy-2-(phenylthio)-alpha-glucotrichloro-acetimidate 8. The alpha-D-E glycosidic linkage was introduced by using 2-deoxy-2-iodo-alpha-glycosyl acetate donor 14 as the glycosyl transfer agent.

  DOI：

  10.1021/jo00044a010

文献信息

• Total Synthesis of Olivomycin A
  作者：William R. Roush、Richard A. Hartz、Darin J. Gustin

  DOI：10.1021/ja984229e

  日期：1999.3.1

  aureolic acids are known to bind in the minor groove of double stranded DNA as 2:1 antibiotic:Mg 2+ complexes, with selectivity for GC rich sequences. 5-8 Recently, the GC rich promoter regions of the c-myc protooncogene and the dihydrofolate-reductase gene have been identified as possible biological targets of mithramycin.9,10 We report herein a highly stereoselective total synthesis of olivomycin

  已知月桂酸以 2:1 抗生素：Mg 2+ 复合物的形式结合在双链 DNA 的小沟中，对富含 GC 的序列具有选择性。5-8 最近，c-myc 原癌基因和二氢叶酸还原酶基因的富含 GC 的启动子区域已被鉴定为光神霉素的可能生物靶标。 9,10 我们在此报告了橄榄霉素 A 的高度立体选择性全合成，构成了第一个月桂酸组任何成员的化学合成。11
• Iodoacetoxylation of Glycals Using Cerium(IV) Ammonium Nitrate, Sodium Iodide, and Acetic Acid:  Stereoselective Synthesis of 2-Deoxy-2-iodo-α-mannopyranosyl Acetates
  作者：William R. Roush、Sridhar Narayan、Chad E. Bennett、Karin Briner

  DOI：10.1021/ol990815g

  日期：1999.9.1

  [formula: see text] The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-alpha-mannopyranosyl acetates with good stereoselectivity. In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iodosuccinimide and HOAc.

  乙酸与硝酸铈（IV）铵盐和碘化钠在乙酸存在下的反应，可得到具有良好立体选择性的2-脱氧-2-碘-α-甘露吡喃糖基乙酸酯。在大多数检查的情况下，其选择性明显优于使用N-碘代琥珀酰亚胺和HOAc的反应。
• Solid-Phase Synthesis of 6-Deoxyoligosaccharides
  作者：J. A. Hunt、William R. Roush

  DOI：10.1021/ja962128f

  日期：1996.1.1