methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate | 320343-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
• 英文别名: methyl (2R,4R,5R,6R)-6-[(1R)-2-hydroxy-1-phenylmethoxyethyl]-2-methoxy-4,5-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 320343-72-4
• 化学式: C₃₁H₃₆O₈
• 分子量: 536.622
• InChiKey: GKVDMVJBWRMRLH-IPVPECPMSA-N

物化性质

• 沸点：
  652.7±55.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal

  摘要：

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00371-2
• 作为产物：
  描述：

  1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-manno-heptitol 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 6.5h， 生成 methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate
  参考文献：
  名称：

  Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal

  摘要：

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00371-2

文献信息

• Synthetic approach to 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) α-disaccharides via a ketene dithioacetal
  作者：Jacek Młynarski、Anna Banaszek

  DOI：10.1016/s0957-4166(00)00371-2

  日期：2000.9

  A unique strategy for the synthesis of Kdo cc-disaccharides based on the ketene dithioacetal 4 (precursor of Kdo) as a 'glycosyl donor' has been developed. Direct, fully stereoselective addition of 6-, 7-, or 8-OH unprotected sugar units to the exo-anomeric double bond in 4, promoted by trimethylsilyl triflate, led to the corresponding O-disaccharides 12 with the dithioacetal residue intact. Subsequent hydrolysis of the later afforded the title compounds in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.