benzyl (2S)-2-(phenylmethoxycarbonylamino)-3-phosphonooxypropanoate | 62293-18-9

• 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: benzyl (2S)-2-(phenylmethoxycarbonylamino)-3-phosphonooxypropanoate
• CAS: 62293-18-9
• 化学式: C₁₈H₂₀NO₈P
• 分子量: 409.332
• InChiKey: WFPSDODNDLRQGN-INIZCTEOSA-N

物化性质

• 熔点：
  119 °C
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-2-(phenylmethoxycarbonylamino)-3-phosphonooxypropanoate 、 2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 silver carbonate 作用下， 以 甲苯 为溶剂， 以45%的产率得到benzyl (2S)-3-bis[[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy]phosphoryloxy-2-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Synthesis of bis-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-l-serinyl phosphate, as a prodrug of mannose-1-phosphate

  摘要：

  An efficient synthesis of di-mannosyl serinyl phosphate using a convergent strategy involving a silver assisted nucleophilic substitution of tetra-O-acetyl-alpha-D-mannopyranosyl bromide by a conveniently protected O-serinyl phosphate is described. The straightforward synthesis of phosphoserine under Mitsunobu conditions is also reported. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.09.023
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酸苯醚 在 四氮唑 、 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzyl (2S)-2-(phenylmethoxycarbonylamino)-3-phosphonooxypropanoate
  参考文献：
  名称：

  Synthesis of bis-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-l-serinyl phosphate, as a prodrug of mannose-1-phosphate

  摘要：

  An efficient synthesis of di-mannosyl serinyl phosphate using a convergent strategy involving a silver assisted nucleophilic substitution of tetra-O-acetyl-alpha-D-mannopyranosyl bromide by a conveniently protected O-serinyl phosphate is described. The straightforward synthesis of phosphoserine under Mitsunobu conditions is also reported. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.09.023

文献信息

• PAQUET, ALENKA;JOHNS, MICHAEL, INT. J. PEPTIDE AND PROTEIN RES., 36,(1990) N, C. 97-103
  作者：PAQUET, ALENKA、JOHNS, MICHAEL

  DOI：——

  日期：——
• Synthesis of bis-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-l-serinyl phosphate, as a prodrug of mannose-1-phosphate
  作者：Amira Khaled、Christine Gravier-Pelletier、Yves Le Merrer

  DOI：10.1016/j.tetasy.2007.09.023

  日期：2007.9

  An efficient synthesis of di-mannosyl serinyl phosphate using a convergent strategy involving a silver assisted nucleophilic substitution of tetra-O-acetyl-alpha-D-mannopyranosyl bromide by a conveniently protected O-serinyl phosphate is described. The straightforward synthesis of phosphoserine under Mitsunobu conditions is also reported. (c) 2007 Published by Elsevier Ltd.