3,6,2',3',4',6'-hexa-O-benzyl-2-(Z)-butadienyl-D-lactal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6,2',3',4',6'-hexa-O-benzyl-2-(Z)-butadienyl-D-lactal
• 英文别名: (2R,3S,4R)-5-[(1Z)-buta-1,3-dienyl]-4-phenylmethoxy-2-(phenylmethoxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran
• 化学式: C₅₈H₆₀O₉
• 分子量: 901.109
• InChiKey: GEGWMMVWGVYPOO-VLQLCKDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  hexa-O-benzyl lactal 在 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 52.17h， 生成 3,6,2',3',4',6'-hexa-O-benzyl-2-(Z)-butadienyl-D-lactal
  参考文献：
  名称：

  Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-(β-Methyl)Methylene Glycosides

  摘要：

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.

  DOI：

  10.1080/07328300008544109

文献信息

• Glycosidation of 3,4,6-Tri-<i>O</i>-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-<i>C</i>-(β-Methyl)Methylene Glycosides
  作者：Ben-Ami Feit、Idil Kasuto Kelson、Anke Gerull、Sarah Abramson、Richard R. Schmidt

  DOI：10.1080/07328300008544109

  日期：2000.1

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.