methyl 3-deoxy-2,5-bis-O-di-tert-butylsilyl-3-C-methylene-α-D-arabinofuranoside | 440359-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: methyl 3-deoxy-2,5-bis-O-di-tert-butylsilyl-3-C-methylene-α-D-arabinofuranoside
• 英文别名: (1S,6S,8S)-3,3-ditert-butyl-8-methoxy-9-methylidene-2,4,7-trioxa-3-silabicyclo[4.2.1]nonane
• CAS: 440359-28-4
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: WLMOECJCVMMUIS-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-deoxy-2,5-bis-O-di-tert-butylsilyl-3-C-methylene-α-D-arabinofuranoside 在 三乙烯二胺 、 咪唑 、 ruthenium trichloride 、 sodium periodate 、 氢氟酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.5h， 生成 methyl 5-O-tert-butyldimethylsilyl-3-C-hydroxymethyl-6-O-(4-toluene)sulfonyl-α-D-arabinofuranoside
  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
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-lyxofuranoside 在 palladium dihydroxide 吡啶 、 4 A molecular sieve 、 氢气 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯甲醇 为溶剂， 反应 100.0h， 生成 methyl 3-deoxy-2,5-bis-O-di-tert-butylsilyl-3-C-methylene-α-D-arabinofuranoside
  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

文献信息

• Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis
  作者：Justin B. Houseknecht、Todd L. Lowary

  DOI：10.1021/jo011127p

  日期：2002.6.1

  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.