methyl 2-O-allyl-3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate | 271245-03-5

• 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 2-O-allyl-3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate
• CAS: 271245-03-5
• 化学式: C₂₅H₃₂O₁₀
• 分子量: 492.523
• InChiKey: QICXSGCSDWZHOC-BQVOVUJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-allyl-3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate 在 四(三苯基膦)钯 、 三正丁基氢锡 、 zinc(II) chloride 、 2-甲氧基丙烯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 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：

  在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 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