(1R)-1,5-anhydro-3,4,6-tri-O-benzyl-1-(2-butynyl)-2-deoxy-D-arabino-hexitol | 1021954-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1,5-anhydro-3,4,6-tri-O-benzyl-1-(2-butynyl)-2-deoxy-D-arabino-hexitol
• CAS: 1021954-55-1
• 化学式: C₃₁H₃₄O₄
• 分子量: 470.609
• InChiKey: XSCCMPLHMYIYDF-VTMRUAGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R)-1,5-anhydro-3,4,6-tri-O-benzyl-1-(2-butynyl)-2-deoxy-D-arabino-hexitol 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以58%的产率得到5,9-anhydro-7,8,10-tri-O-benzyl-1,4,6-trideoxy-D-manno-deco-2,3-diulose
  参考文献：
  名称：

  Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates

  摘要：

  Photolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening, of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.

  DOI：

  10.1021/jo702663w
• 作为产物：
  描述：

  、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.67h， 以58%的产率得到(1R)-1,5-anhydro-3,4,6-tri-O-benzyl-1-(2-butynyl)-2-deoxy-D-arabino-hexitol
  参考文献：
  名称：

  Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates

  摘要：

  Photolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening, of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.

  DOI：

  10.1021/jo702663w