methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-7-ynopyranoside | 1021954-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-7-ynopyranoside
• CAS: 1021954-46-0
• 化学式: C₃₁H₃₄O₅
• 分子量: 486.608
• InChiKey: QVYPUJWZCIAJSV-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  36.0
• 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：
  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：

  methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-7-ynopyranoside 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以49%的产率得到methyl 2,3,4-tri-O-benzyl-6,9-dideoxy-α-D-gluco-nonopyranoside-7,8-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：

  methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-8-ynopyranoside 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以70%的产率得到methyl 2,3,4-tri-O-benzyl-6,7,8,9-tetradeoxy-α-D-gluco-non-7-ynopyranoside
  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