3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride | 1017587-59-5

• 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: 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride
• 英文别名: 2,2,2-trichloro-N-[(2R,3R,4R,5S,6R)-2-fluoro-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 1017587-59-5
• 化学式: C₂₂H₂₃Cl₃FNO₅
• 分子量: 506.786
• InChiKey: COZFSXKZJYUDQW-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride 、 苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 在 4 A molecular sieve 、 sulfobromophthalein sodium 、 三氟甲磺酸酐 作用下， 以 various solvent(s) 为溶剂， 反应 0.67h， 生成 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation

  摘要：

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.029
• 作为产物：
  描述：

  在 吡啶 作用下， 以 水 为溶剂， 反应 1.0h， 以35.5 mg的产率得到3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation

  摘要：

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.029

文献信息

• Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation
  作者：Akiharu Ueki、Masafumi Hirota、Yuta Kobayashi、Keiko Komatsu、Yutaka Takano、Michio Iwaoka、Yuko Nakahara、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2008.01.029

  日期：2008.3

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.