1-bromo-(2,3,4,6-tetra-O-isobutyryl)-α-D-mannopyranose | 926646-33-5

• 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: 1-bromo-(2,3,4,6-tetra-O-isobutyryl)-α-D-mannopyranose
• CAS: 926646-33-5
• 化学式: C₂₂H₃₅BrO₉
• 分子量: 523.418
• InChiKey: VKDDXNLVMHFZPD-ZBRFXRBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-bromo-(2,3,4,6-tetra-O-isobutyryl)-α-D-mannopyranose 、 disilver phenyl phosphate 以 甲苯 为溶剂， 反应 18.0h， 生成 Isobutyric acid (2R,3S,4S,5R,6R)-4,5-bis-isobutyryloxy-6-isobutyryloxymethyl-2-[phenoxy-((2R,3S,4S,5R,6R)-3,4,5-tris-isobutyryloxy-6-isobutyryloxymethyl-tetrahydro-pyran-2-yloxy)-phosphoryloxy]-tetrahydro-pyran-3-yl ester
  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：

  甘露糖 、 异丁酸酐 在 4-二甲氨基吡啶 、 三乙胺 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到1-bromo-(2,3,4,6-tetra-O-isobutyryl)-α-D-mannopyranose
  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

文献信息

• MANNOSYL-1 PHOSPHATES, PREPARATION METHOD AND THERAPEUTIC USE, IN PARTICULAR AGAINST THE CDG-IA SYNDROME
  申请人：Gravier-Pelletier Christine

  公开号：US20090054353A1

  公开（公告）日：2009-02-26

  The present invention relates, as medicaments, to the α-D-mannopyranosyl-1 phosphate derivatives of formulae I, II and III: (where each group R 11 to R 14 , R 21 to R 24 , R 31 to R 34 is H or an OH-protective group, and R and R′ are defined as indicated in the description), which can be used as cellular sources of Man-1 P, against the CDG-I syndrome and in particular the CDG-Ia syndrome. The invention also relates to these derivatives as industrial products and to their method of preparation.

  本发明涉及α-D-甘露糖基-1磷酸衍生物（式I、II和III），作为药物使用：（其中每个基团R11到R14，R21到R24，R31到R34是H或OH保护基，R和R'如说明中所示），可以用作Man-1 P的细胞来源，用于对抗CDG-I综合征，特别是CDG-Ia综合征。本发明还涉及这些衍生物作为工业产品及其制备方法。