benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-β-D-galactopyranoside | 78120-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-β-D-galactopyranoside
• 英文别名: benzyl 3,4-O-isopropylidene-β-D-fucopyranoside
• CAS: 78120-07-7
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: BXRQMPTUCSZNJD-TVKJYDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-β-D-galactopyranoside 、 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranose 1-trichloroacetimidate 在 silver trifluoromethanesulfonate 作用下， 以50%的产率得到1-benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside
  参考文献：
  名称：

  A comparative analysis of mono- and disaccharide benzyl fucopyranosides

  摘要：

  The syntheses and X-ray analyses of two fucopyranosides, the monosaccharide benzyl 3,4-di-O-acetyl-2-hydroxy-beta-D-fucopyranoside, C17H22O7, and the disaccharide 1-benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 2)3,4-O-isopropylidene-beta-D-fucopyranoside, C33H40O12, are described. The different substituents induce small conformational changes on the fucopyranoside ring. However, the conformation of the benzyl group varies from (+)gauche for the monosaccharide to synperiplanar for the disaccharide.

  DOI：

  10.1107/s0108270102012556
• 作为产物：
  描述：

  D-Fucose 在 盐酸 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 benzyl 6-deoxy-3,4-O-isopropylidene-6-phenylthio-β-D-galactopyranoside
  参考文献：
  名称：

  A comparative analysis of mono- and disaccharide benzyl fucopyranosides

  摘要：

  The syntheses and X-ray analyses of two fucopyranosides, the monosaccharide benzyl 3,4-di-O-acetyl-2-hydroxy-beta-D-fucopyranoside, C17H22O7, and the disaccharide 1-benzyl O-(2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranosyl)-(1 --> 2)3,4-O-isopropylidene-beta-D-fucopyranoside, C33H40O12, are described. The different substituents induce small conformational changes on the fucopyranoside ring. However, the conformation of the benzyl group varies from (+)gauche for the monosaccharide to synperiplanar for the disaccharide.

  DOI：

  10.1107/s0108270102012556

文献信息

• Preparation of carbohydrate isopropylidene derivatives with 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid
  作者：András Lipták、János Imre、Pál Nánási

  DOI：10.1016/s0008-6215(00)85991-1

  日期：——