methyl 3-C-acetyl-3,6-anhydro-2-deoxy-7-O-methyl-4,5-O-isopropylidene-D-altro-heptonate | 1021954-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 3-C-acetyl-3,6-anhydro-2-deoxy-7-O-methyl-4,5-O-isopropylidene-D-altro-heptonate
• 英文别名: methyl 2-[(3aR,4R,6R,6aR)-4-acetyl-6-(methoxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]acetate
• CAS: 1021954-40-4
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: UUXSYDFXFQKORG-LHMODEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 (6R,7S,8R)-1-hydroxy-7,8-O-isopropylidene-6-(methoxymethyl)-1-methyl-5-oxaspiro[3.4]octan-2-one 在 过碘酸 作用下， 反应 2.0h， 生成 methyl 3-C-acetyl-3,6-anhydro-2-deoxy-7-O-methyl-4,5-O-isopropylidene-D-allo-heptonate 、 methyl 3-C-acetyl-3,6-anhydro-2-deoxy-7-O-methyl-4,5-O-isopropylidene-D-altro-heptonate
  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

文献信息

• Stereocontrolled Photocyclization of 1,2-Diketones: Application of a 1,3-Acetyl Group Transfer Methodology to Carbohydrates
  作者：Antonio J. Herrera、María Rondón、Ernesto Suárez

  DOI：10.1021/jo702663w

  日期：2008.5.1

  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.