1,5-anhydro-4-O-isobutyryl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol | 142841-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-4-O-isobutyryl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol
• 英文别名: [(2S,3S,4S)-4-hydroxy-2,4-dimethyl-2,3-dihydropyran-3-yl] 2-methylpropanoate
• CAS: 142841-35-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: HOCJPSSZVWCJDH-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4-O-isobutyryl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 、 sodium iodide 作用下， 以 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 、 异丁酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到1,5-anhydro-4-O-isobutyryl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

  摘要：

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.

  DOI：

  10.1021/jo900131a

文献信息

• 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。
• 2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1021/jo900131a

  日期：2009.3.20

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.
• Synthesis of C-D-E trisaccharide precursors of olivomycin A.
  作者：David P. Sebesta、William R. Roush

  DOI：10.1021/jo00044a010

  日期：1992.8

  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.