methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyran-ose)onate | 142644-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyran-ose)onate
• 英文别名: methyl 2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosonate；methyl (2S,4S,5R,6R)-2,4,5-triacetyloxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 142644-34-6
• 化学式: C₂₂H₃₀O₁₅
• 分子量: 534.471
• InChiKey: CDJOMBIWROBESK-ZJGVECAJSA-N

物化性质

• 沸点：
  540.5±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  193.33
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R,6S)-1,2:4,5-di-O-isopropylidene-non-8-yne-1,2,3,4,5,6-hexol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 臭氧 、 silver nitrate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 49.75h， 生成 methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate 、 methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyran-ose)onate
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t

文献信息

• Studies on Sialic Acid. Part XXVII. Synthesis and Characterization of Furanose and Pyranose Derivatives of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).
  作者：Mitsunobu NAKAMURA、Hiroaki TAKAYANAGI、Kimio FURUHATA、Haruo OGURA

  DOI：10.1248/cpb.40.879

  日期：——

  The products of Fischer's methyl glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) revealed existence of an the anomeric equilibrium between α, β-furanose and α, β-pyranose of KDN. In spite of the anomeric equilibrium, peracetylation of KDN and its derivatives by acetic anhydride with pyridine gave only α- and β-pyranose derivatives. The obtained methyl glycosides and hexa-O-acetyl derivatives were characterized by X-ray, nuclear magnetic resonance and cicular dichroism spectral analyses.

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)的费舍尔甲基糖基化产物表明，KDN 的 α, β-呋喃糖和 α, β-吡喃糖之间存在着异构体平衡。尽管存在同分异构平衡，但用乙酸酐与吡啶对 KDN 及其衍生物进行过乙酰化反应只能得到 α 和 β-吡喃糖衍生物。获得的甲基苷和六-O-乙酰基衍生物通过 X 射线、核磁共振和立体二色光谱分析进行了表征。
• AUGE, CLAUDINE;GAUTHERON, CHRISTINE;DAVID, SERGE;MALLERON, ANNIE;CAVAYE, +, TETRAHEDRON, 46,(1990) N, C. 201-214
  作者：AUGE, CLAUDINE、GAUTHERON, CHRISTINE、DAVID, SERGE、MALLERON, ANNIE、CAVAYE, +

  DOI：——

  日期：——