2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9,10-tetradeoxy-D-glycero-L-gulo-dec-8-ynitol | 1021954-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9,10-tetradeoxy-D-glycero-L-gulo-dec-8-ynitol
• CAS: 1021954-21-1
• 化学式: C₃₈H₄₀O₅
• 分子量: 576.733
• InChiKey: KGQQEPZEGPZMJZ-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9,10-tetradeoxy-D-glycero-L-gulo-dec-8-ynitol 在 ruthenium(IV) oxide sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 1.5h， 以59%的产率得到5,9-anhydro-6,7,8,10-tetra-O-benzyl-1,4-dideoxy-D-glycero-D-ido-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：

  (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(3,3-dibromoallyl)tetrahydro-2H-pyran 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 以70%的产率得到2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9,10-tetradeoxy-D-glycero-L-gulo-dec-8-ynitol
  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