Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-fluoromethyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester | 153448-95-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-fluoromethyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester
• CAS: 153448-95-4
• 化学式: C₁₂H₁₈FO₁₁P
• 分子量: 388.24
• InChiKey: PHJMLXQJSYCBHX-YBXAARCKSA-N

物化性质

• 沸点：
  496.6±55.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  154.89
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-fluoromethyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester 在 galactosyltransferase 、 HEPES buffer 、 alkaline phosphatase 作用下， 反应 48.0h， 生成 methyl O-(6-deoxy-6-fluoro-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chains

  摘要：

  Glycosylation with chemicallY prepared UDP-6-deoxy-D-galactose and its 6-fluoro analog using bovine (1-4)-beta-D-galactosyltransferase was demonstrated to be effective enough for practical purpose. A biantennary pentasaccharide having two 6'-deoxylactosamine residues was synthesized.

  DOI：

  10.1016/0040-4039(93)85060-a
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-D-galactopyranosyl 1-phosphate dibenzyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-fluoromethyl-2-phosphonooxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of UDP-6-deoxy- and -6-fluoro-D-galactoses and their enzymatic glycosyl transfer to mono- and biantennary carbohydrate chains

  摘要：

  Glycosylation with chemicallY prepared UDP-6-deoxy-D-galactose and its 6-fluoro analog using bovine (1-4)-beta-D-galactosyltransferase was demonstrated to be effective enough for practical purpose. A biantennary pentasaccharide having two 6'-deoxylactosamine residues was synthesized.

  DOI：

  10.1016/0040-4039(93)85060-a