per-O-trimethylsilyl-L-arabinose | 32166-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per-O-trimethylsilyl-L-arabinose
• 英文别名: β-L-arabinopyranose TMS；Tetrakis-O-trimethylsilyl-β-L-arabinose；Arabinopyranose, tetrakis-O-(trimethylsilyl)-, beta-D-；trimethyl-[(2R,3R,4S,5S)-2,3,5-tris(trimethylsilyloxy)oxan-4-yl]oxysilane
• CAS: 32166-73-7
• 化学式: C₁₇H₄₂O₅Si₄
• 分子量: 438.859
• InChiKey: KEOUSSOURMHEKN-MWDXBVQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  per-O-trimethylsilyl-L-arabinose 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides

  摘要：

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).

  DOI：

  10.1080/07328309808001892
• 作为产物：
  描述：

  三甲基氯硅烷 、 L-(+)-arabinose 在 吡啶 作用下， 反应 1.0h， 以100%的产率得到per-O-trimethylsilyl-L-arabinose
  参考文献：
  名称：

  Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides

  摘要：

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).

  DOI：

  10.1080/07328309808001892

文献信息

• Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides
  作者：Taketo Uchiyama、Ole Hindsgaul

  DOI：10.1080/07328309808001892

  日期：1998.11

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).