phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside | 482648-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside
• 英文别名: benzyl 2,3,4-tri-O-acetyl-beta-d-fucopyranoside；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-methyl-6-phenylmethoxyoxan-3-yl] acetate
• CAS: 482648-35-1
• 化学式: C₁₉H₂₄O₈
• 分子量: 380.395
• InChiKey: HJEZYHYUFLWLLL-BBVHWWONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside 在 sodium methylate 作用下， 生成 benzyl 3,4-di-O-acetyl-2-hydroxy-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：

  1,2,3,4-tetra-O-acetyl-D-fucopyranose 在 3 A molecular sieve 、 氢溴酸 、 乙酸酐 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside
  参考文献：
  名称：

  摘要：

  The synthesis and X-ray analysis of the title compound is described. The peracetylated benzyl fucopyranoside derivative was prepared by following the classical Koenigs-Knorr methodology. The X-ray diffraction analysis showed a monoclinic system, with a = 9.7834(5) Angstrom, b = 10.4653(6) Angstrom, c = 10.0752(6) Angstrom, space group P2(1), and beta = 100.1820(1)degrees. Expected C-4(1) conformation was observed for the fucoside ring and benzyl group, which were oriented toward an equatorial position. Endocyclic angle C1-O5-C5 was in agreement with the geometry of equatorial glycoside bonds, typical for beta-D-C-4(1) pyranoside conformation.

  DOI：

  10.1023/a:1020296922224