2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl phosphate | 503312-35-4

• 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: 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl phosphate
• 英文别名: 2,3,4,6-tetra-O-pivaloyl-alfa-D-mannopyranosyl phosphate；pivaloyl(-2)[pivaloyl(-3)][pivaloyl(-4)][pivaloyl(-6)]a-Man1P；[(2R,3R,4S,5S,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-phosphonooxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 503312-35-4
• 化学式: C₂₆H₄₅O₁₃P
• 分子量: 596.609
• InChiKey: PIXWKMOLTJLTQO-DFBDCSAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl phosphate 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以31%的产率得到bis-acetoxymethyl-(2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl)-phosphate
  参考文献：
  名称：

  Membrane-Permeant derivatives of mannose-1-phosphate

  摘要：

  For treatment of congenital disorder of glycosylation type Ia membrane-permeant dcrivatives of mannose-1-phosphate are required. Employing biologically cleavable phosphate protecting groups advantageous precursor derivatives could be synthesized following a facile approach. Their enzymatic cleavages using esterase from porcine liver (E.C. 3.1.1.1) were investigated. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00269-9
• 作为产物：
  描述：

  (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 在 palladium on activated charcoal 吡啶 、 四氮唑 、 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 4.0h， 生成 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranosyl phosphate
  参考文献：
  名称：

  Membrane-Permeant derivatives of mannose-1-phosphate

  摘要：

  For treatment of congenital disorder of glycosylation type Ia membrane-permeant dcrivatives of mannose-1-phosphate are required. Employing biologically cleavable phosphate protecting groups advantageous precursor derivatives could be synthesized following a facile approach. Their enzymatic cleavages using esterase from porcine liver (E.C. 3.1.1.1) were investigated. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00269-9

文献信息

• Membrane-Permeant derivatives of mannose-1-phosphate
  作者：Synke Rutschow、Joachim Thiem、Christian Kranz、Thorsten Marquardt

  DOI：10.1016/s0968-0896(02)00269-9

  日期：2002.12

  For treatment of congenital disorder of glycosylation type Ia membrane-permeant dcrivatives of mannose-1-phosphate are required. Employing biologically cleavable phosphate protecting groups advantageous precursor derivatives could be synthesized following a facile approach. Their enzymatic cleavages using esterase from porcine liver (E.C. 3.1.1.1) were investigated. (C) 2002 Published by Elsevier Science Ltd.