methyl (3-O-acetyl-4,5;7,8-di-O-isopropylidene-D-glycero-α-D-galacto-oct-2-ulopyranosyl)onate | 271245-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3-O-acetyl-4,5;7,8-di-O-isopropylidene-D-glycero-α-D-galacto-oct-2-ulopyranosyl)onate
• 英文别名: methyl 3-O-acetyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-galacto-2-octulopyranosonate；methyl (3aS,4R,6R,7R,7aS)-7-acetyloxy-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
• CAS: 271245-00-2
• 化学式: C₁₇H₂₆O₁₀
• 分子量: 390.387
• InChiKey: OGHMBJJXKAVWTG-KABUYRKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (3-O-acetyl-4,5;7,8-di-O-isopropylidene-D-glycero-α-D-galacto-oct-2-ulopyranosyl)onate 在 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 44.5h， 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
• 作为产物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 在 吡啶 、 N-碘代丁二酰亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.5h， 生成 methyl (3-O-acetyl-4,5;7,8-di-O-isopropylidene-D-glycero-α-D-galacto-oct-2-ulopyranosyl)onate
  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

文献信息

• Synthesis of α-d-glucosyl substituted methyl glycosides of 3-deoxy-α-d-manno- and d-glycero-α-d-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
  作者：Barbara Pokorny、Sven Müller-Loennies、Paul Kosma

  DOI：10.1016/j.carres.2014.03.004

  日期：2014.6

  The alpha-d-glucopyranosyl-(1-->5)-substituted methyl glycosides of 3-deoxy-alpha-d-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-alpha-d-lyxo-hept-2-ulosonic acid (Kdh), and d-glycero-alpha-d-talo-oct-2-ulosonic acid (Ko) were prepared using orthogonally protected glycosyl acceptor derivatives via glycosylation with a torsionally disarmed 4,6-O-benzylidene protected trifluoroacetimidate glucosyl donor

  3-deoxy-alpha-d-manno-oct-2-ulosonic acid (Kdo)、3-deoxy-alpha-d-lyxo-hept 的 α-d-吡喃葡萄糖基-(1-->5)-取代的甲基糖苷-2-ulosonic 酸 (Kdh) 和 d-glycero-alpha-d-talo-oct-2-ulosonic 酸 (Ko) 是使用正交保护的糖基受体衍生物通过糖基化与扭转解除武装的 4,6-O-亚苄基制备的受保护的三氟乙酰亚胺酯葡萄糖基供体，然后进行整体去保护。相关的 6-O-磷酰基-α-d-吡喃葡萄糖基-(1-->5)-取代的 Kdo 和 Kdh 衍生物分别来自使用亚磷酰胺和基于磷酰氯的磷酸化步骤的亚苄基保护的葡萄糖基中间体。去保护的二糖作为配体研究不动杆菌脂多糖核心寡糖的凝集素结合。