methyl 2,6-anhydro-5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-enonate | 352437-61-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,6-anhydro-5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-enonate
• 英文别名: methyl (2R,3R,4S)-3-azido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 352437-61-7
• 化学式: C₁₀H₁₅N₃O₇
• 分子量: 289.245
• InChiKey: WYCUVEKNVLAKCR-FVDCJOIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,6-anhydro-5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-enonate 在 吡啶 、 四丁基溴化铵 、 二正丁基氧化锡 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 54.5h， 生成 methyl 4-O-acetyl-2,6-anhydro-5-azido-9-O-benzyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-enonate
  参考文献：
  名称：

  Schneider, Regine; Freyhardt, Clemens C.; Schmidt, Richard R., European Journal of Organic Chemistry, 2001, # 9, p. 1655 - 1661

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,7,8,9-Penta-O-acetyl-5-azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 methyl 2,6-anhydro-5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-enonate
  参考文献：
  名称：

  2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae

  摘要：

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.

  DOI：

  10.1016/0008-6215(92)84150-q

文献信息

• Facile synthesis of C5-azido derivatives of thiosialosides and 2,3-dehydro-5-N-acetylneuraminic acid (DANA)
  作者：Mostafa Radwan、Manas Jana、Christopher W Cairo

  DOI：10.1016/j.carres.2023.109013

  日期：2024.2

  Neuraminic acid (Neu5Ac, also known as sialic acid) is an important monosaccharide found in glycoproteins and glycolipids which plays a vital role in regulation of physiological functions and pathological conditions. The study of sialoglycans has benefitted from the development of glycomimetic probes and inhibitors for proteins and enzymes that interact with and modify neuraminic acid in glycan chains

  神经氨酸（Neu5Ac，又称唾液酸）是糖蛋白和糖脂中发现的重要单糖，在调节生理功能和病理状态中发挥着重要作用。唾液酸聚糖的研究受益于与聚糖链中的神经氨酸相互作用并修饰其的蛋白质和酶的糖模拟探针和抑制剂的开发。需要高产率获取唾液酸苷中间体的方法来促进新靶标的设计。在这里，我们报道了使用温和的方法对 C5-乙酰胺基官能团进行脱保护，然后使用重氮基转移试剂合成 C5-叠氮基硫唾液酸苷。我们研究了两种重氮转移策略并比较了它们的产率和乙酸盐保护基团的耐受性。还对通常用于生成神经氨酸酶（唾液酸酶）抑制剂的2,3-脱氢-5- N-乙酰神经氨酸（DANA）支架进行了相同的方法和比较。我们发现硫唾液酸苷和 DANA 的 C5-叠氮衍生物可以通过五步或六步生产，产率分别高达 76% 和 83%。本研究中比较的重氮转移试剂是三氟甲磺酰叠氮化物（TfN 3 ）和咪唑-1-磺酰叠氮化物（ImzSO 2 N 3 ）。
• 2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae
  作者：Erwin Schreiner、Erich Zbiral、Reinhard G. Kleineidam、Roland Schauer

  DOI：10.1016/0008-6215(92)84150-q

  日期：1992.9

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.
• Schneider, Regine; Freyhardt, Clemens C.; Schmidt, Richard R., European Journal of Organic Chemistry, 2001, # 9, p. 1655 - 1661
  作者：Schneider, Regine、Freyhardt, Clemens C.、Schmidt, Richard R.

  DOI：——

  日期：——