methyl 3-O-benzoyl-2-deoxy-2-ethylthio-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate | 271245-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-O-benzoyl-2-deoxy-2-ethylthio-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate
• CAS: 271245-06-8
• 化学式: C₂₄H₃₂O₉S
• 分子量: 496.579
• InChiKey: XILKHHAPJWWSOG-YGVAAJGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzoyl-2-deoxy-2-ethylthio-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 methyl 3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate 、 methyl 3-O-benzoyl-4,5:7,8-di-O-isopropylidene-β-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 在 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 硼烷铵络合物 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 35.0h， 生成 methyl 3-O-benzoyl-2-deoxy-2-ethylthio-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