5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-vinyl-β-D-lyxofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-vinyl-β-D-lyxofuranoside
• 英文别名: (3aS,5R,6S,6aS)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-ethenyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• 化学式: C₂₆H₃₄O₅Si
• 分子量: 454.638
• InChiKey: OOFQYTIGVLTNRB-ONJIFJTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-vinyl-β-D-lyxofuranoside
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p