2,4,7,8,9-Penta-O-acetyl-5-azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester | 126695-28-1

• 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: 2,4,7,8,9-Penta-O-acetyl-5-azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester
• 英文别名: methyl 2,4,7,8,9-penta-O-acetyl-5-azido-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate；methyl 2,4,7,8,9-penta-O-acetyl-5-azido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonate；methyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate；methyl (2R,4S,5R,6R)-2,4-diacetyloxy-5-azido-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 126695-28-1
• 化学式: C₂₀H₂₇N₃O₁₃
• 分子量: 517.447
• InChiKey: WWIHGYZUOMDBEE-DCDDNHAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  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 silver carbonate 盐酸 作用下， 以 乙醚 为溶剂， 反应 17.0h， 生成 Methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester
  参考文献：
  名称：

  Schrell, Andreas; Whitesides, George M., Liebigs Annalen der Chemie, 1990, # 11, p. 1111 - 1114

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 5-Azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester 在 吡啶 作用下， 以92%的产率得到2,4,7,8,9-Penta-O-acetyl-5-azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid methyl ester
  参考文献：
  名称：

  Schrell, Andreas; Whitesides, George M., Liebigs Annalen der Chemie, 1990, # 11, p. 1111 - 1114

  摘要：

  DOI：

文献信息

• Microbial Glycosyltransferases for Carbohydrate Synthesis:  α-2,3-Sialyltransferase from <i>Neisseria </i><i>g</i><i>onorrheae</i>
  作者：Masayuki Izumi、Gwo-Jenn Shen、Shirley Wacowich-Sgarbi、Takuji Nakatani、Oliver Plettenburg、Chi-Huey Wong

  DOI：10.1021/ja011382r

  日期：2001.11.1

  exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharides, glycolipids, and glycopeptides and their sulfate derivatives. Some CMP-sialic acid derivatives with modification at the C-5 position were also prepared for evaluation as donor substrates. It was found that the enzyme exhibits a broader

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，
• 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.
• Schreiner, Erwin; Zbiral, Erich, Liebigs Annalen der Chemie, 1990, # 6, p. 581 - 586
  作者：Schreiner, Erwin、Zbiral, Erich

  DOI：——

  日期：——
• Kuznik; Unverzagt, Carlo; Hoersch, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 745 - 752
  作者：Kuznik、Unverzagt, Carlo、Hoersch、Kretzschmar

  DOI：——

  日期：——
• SCHRELL, ANDREAS;WHITESIDES, GEORGE M., LIEBIGS ANN. CHEM.,(1990) N1, C. 1111-1114
  作者：SCHRELL, ANDREAS、WHITESIDES, GEORGE M.

  DOI：——

  日期：——