[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[phenylmethoxy-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]oxyoxan-2-yl]methyl acetate | 926646-20-0

• 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: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[phenylmethoxy-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]oxyoxan-2-yl]methyl acetate
• CAS: 926646-20-0
• 化学式: C₃₅H₄₅O₂₂P
• 分子量: 848.703
• InChiKey: MFWHHISXRNKUDN-RGPVJJJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  58
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  274
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[phenylmethoxy-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]oxyoxan-2-yl]methyl acetate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以60%的产率得到[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[hydroxy-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Mono, di and tri-mannopyranosyl phosphates as mannose-1-phosphate prodrugs for potential CDG-Ia therapy

  摘要：

  An efficient and convergent method for the synthesis of mannose-1-phosphate prodrugs is described as a potential therapy for congenital disorders of glycosylation-la (CDG-Ia). The key feature of the proposed approach is the silver assisted nucleophilic substitution of 2,3,4,6-tetra-O-protected-alpha-D-mannopyranosyl bromides with various silver phosphate salts to afford mono, di, and tri-mannopyranosyl phosphates. A preliminary biological evaluation of the synthesized phosphate prodrugs has been carried out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.074
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 氢溴酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[phenylmethoxy-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphosphoryl]oxyoxan-2-yl]methyl acetate
  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