methyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate diethyldithioacetal | 271244-97-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate diethyldithioacetal
• 英文别名: methyl (3R)-3-[(4R,5S)-5-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(ethylsulfanyl)-3-hydroxypropanoate
• CAS: 271244-97-4
• 化学式: C₁₉H₃₄O₈S₂
• 分子量: 454.606
• InChiKey: WOZRSZBUCCAVTA-NIFZNCRKSA-N

物化性质

• 沸点：
  588.4±50.0 °C(predicted)
• 密度：
  1.224±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate diethyldithioacetal 在 N-碘代丁二酰亚胺 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以76%的产率得到methyl 4,5:7,8-di-O-isopropylidene-α-D-glycero-D-galacto-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 、 glyoxylic acid methyl ester diethyl mercaptal 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methyl 2-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octulosonate diethyldithioacetal
  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 3-deoxy-d-manno-2-octulosonic acid (Kdo) and d-glycero-d-talo-2-octulosonic acid (Ko) and their α-glycosides
  作者：Martin Reiner、Richard R. Schmidt

  DOI：10.1016/s0957-4166(99)00557-1

  日期：2000.1

  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.