ethyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal | 271244-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal
• CAS: 271244-96-3
• 化学式: C₁₉H₃₂O₈S₂
• 分子量: 452.59
• InChiKey: YYWJMRSFDGBOMN-NIFZNCRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硼烷铵络合物 、 sodium methylate 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 47.55h， 生成 methyl 2-O-allyl-3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate
  参考文献：
  名称：

  Synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo) and d-glycero-d-talo-2-octulosonic acid (Ko) and their α-glycosides

  摘要：

  Reaction of 2,3:5,6-di-O-isopropylidene-D-mannofuranose 1 with C-2 lithio derivatives of glyoxylate mercaptal in the presence of MgBr2 afforded D-glycero-D-galacto-2-octulosonates 2 and 3, respectively. Their 3-O-deoxygenation led to Kdo. N-Iodosuccinimide treatment of 3 gave thioglycoside 11 directly, which was transformed into Ko derivative 12 via epimerisation of the 3-hydroxy group. 3-O-Benzoylation of 12 and then transformation into phosphite furnished 15, an efficient glycosyl donor. Reaction of 15 with 6-O-unprotected glucosamine derivative 22 as acceptor gave alpha-glycoside 23, which was successfully transformed either into Kdo-disaccharide 27 or into Ko-disaccharide 29. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00557-1
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 、 1,3-二噻烷-2-甲酸乙酯 在 lithium diisopropyl amide 、 magnesium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.0h， 以76%的产率得到ethyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate 1,3-propylene dithioacetal
  参考文献：
  名称：

  Synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo) and d-glycero-d-talo-2-octulosonic acid (Ko) and their α-glycosides

  摘要：

  Reaction of 2,3:5,6-di-O-isopropylidene-D-mannofuranose 1 with C-2 lithio derivatives of glyoxylate mercaptal in the presence of MgBr2 afforded D-glycero-D-galacto-2-octulosonates 2 and 3, respectively. Their 3-O-deoxygenation led to Kdo. N-Iodosuccinimide treatment of 3 gave thioglycoside 11 directly, which was transformed into Ko derivative 12 via epimerisation of the 3-hydroxy group. 3-O-Benzoylation of 12 and then transformation into phosphite furnished 15, an efficient glycosyl donor. Reaction of 15 with 6-O-unprotected glucosamine derivative 22 as acceptor gave alpha-glycoside 23, which was successfully transformed either into Kdo-disaccharide 27 or into Ko-disaccharide 29. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00557-1