dimethyl 5-C-acetyl-2,3-di-O-benzyl-4,6-dideoxy-α-D-xylo-heptopyranosiduronate | 1021954-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 5-C-acetyl-2,3-di-O-benzyl-4,6-dideoxy-α-D-xylo-heptopyranosiduronate
• 英文别名: methyl 2-[(2S,4S,5R,6S)-2-acetyl-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]acetate
• CAS: 1021954-36-8
• 化学式: C₂₅H₃₀O₇
• 分子量: 442.509
• InChiKey: NKNGUEYKTRLJRA-VHXCZSFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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 、 (6S,7R,8S)-7,8-bis(benzyloxy)-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-2-one 在 过碘酸 作用下， 反应 2.0h， 生成 dimethyl 5-C-acetyl-2,3-di-O-benzyl-4,6-dideoxy-α-D-xylo-heptopyranosiduronate 、 dimethyl 5-C-acetyl-2,3-di-O-benzyl-4,6-dideoxy-α-D-xylo-heptopyranosiduronate
  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