methyl 2,3,4-tri-O-benzyl-6,9-dideoxy-α-D-gluco-nonopyranoside-7,8-diulose | 952607-10-2

• 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-6,9-dideoxy-α-D-gluco-nonopyranoside-7,8-diulose
• 英文别名: 1-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]butane-2,3-dione
• CAS: 952607-10-2
• 化学式: C₃₁H₃₄O₇
• 分子量: 518.607
• InChiKey: GOTBAUHNOAEFNS-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6,9-dideoxy-α-D-gluco-nonopyranoside-7,8-diulose 以 氯仿 为溶剂， 反应 1.5h， 以100%的产率得到(1R,4R,6S,7R,8S,9S)-7,8,9-tris(benzyloxy)-1-hydroxy-6-methoxy-1-methyl-5-oxaspiro[3.5]nonan-2-one
  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-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

文献信息

• Stereocontrolled Photocyclization of 1,2-Diketones Applied to Carbohydrate Models: A New Entry to <i>C</i>-Ketosides
  作者：Antonio Herrera、Ernesto Suárez、María Rondón

  DOI：10.1055/s-2007-984523

  日期：2007.7

  Photolysis of 1-glycosyl-2,3-butanedione 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 which can be modulated efficiently by using photosensitizers in some

  使用可见光对 1-glycosyl-2,3-butanedione 衍生物进行光解是合成手性 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one 碳水化合物衍生物的温和且选择性的方法。结果强烈表明环化的立体控制取决于构象和立体电子因素，在某些情况下可以通过使用光敏剂进行有效调节。1-羟基-1-甲基-2-环丁酮部分的进一步氧化开放提供了新的C-酮苷衍生物。这个两步过程可以被认为是乙酰基的立体控制的 1,3-转移。