methyl 3,6-di-O-(benzylidene acetal)-2,5-bis-O-tert-butylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside | 440359-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3,6-di-O-(benzylidene acetal)-2,5-bis-O-tert-butylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside
• 英文别名: (1'S,4R,6'R,8'S)-3',3'-ditert-butyl-8'-methoxy-2-phenylspiro[1,3-dioxolane-4,9'-2,4,7-trioxa-3-silabicyclo[4.2.1]nonane]
• CAS: 440359-33-1
• 化学式: C₂₂H₃₄O₆Si
• 分子量: 422.594
• InChiKey: BQOHYRUBPJOLCB-NWBOOGFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,6-di-O-(benzylidene acetal)-2,5-bis-O-tert-butylsilyl-3-C-hydroxymethyl-α-D-arabinofuranoside 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 氢氟酸 、 barium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 Benzoic acid (2R,3S,4S,5S)-3-bromomethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methoxy-tetrahydro-furan-3-yl ester
  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 、 ruthenium trichloride 、 sodium periodate 、 4 A molecular sieve 、 氢气 、 sodium acetate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 、 苯甲醇 为溶剂， 反应 118.5h， 生成 methyl 3,6-di-O-(benzylidene acetal)-2,5-bis-O-tert-butylsilyl-3-C-hydroxymethyl-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.