methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate | 130525-59-6

• 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 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate
• 英文别名: methyl (2R,3R,4R)-3-acetamido-4-azido-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 130525-59-6
• 化学式: C₁₈H₂₄N₄O₁₀
• 分子量: 456.409
• InChiKey: ANKWFOHGBMGGAL-LMHBHQSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以75%的产率得到(2R,3R,4R)-methyl 3-acetamido-4-amino-2-((1S,2R)-1,2,3-triacetoxylpropyl)-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  3-acetamido-4-amino-3,4-dihydro-2H-pyran-6-carboxylates 及其乙酰基迁移异构体的合成和 1H NMR 数据归属

  摘要：

  摘要 在施陶丁格还原制备扎那米韦的4( R )-差向异构体和辛酸拉尼米韦作为原料药杂质的产物中发现了意想不到的乙酰基迁移。(3 R,4R)或(3 R,4S)- 3-acetamido-4-amino-3,4-dihydro-2 H -pyran-6-carboxylates 和乙酰基迁移的合成和1 H NMR 数据归属异构体（3R，4R） - 3-氨基-4-乙酰氨基-3,4-二氢-2 ħ吡喃-6-羧酸酯在本文中描述。此外，实验表明乙酰迁移倾向于在中性或酸性条件下发生，但在碱性条件下不会发生。筛选一些有机碱以阻止迁移过程中的迁移Staudinger减少，并确定最佳 (DBU)。

  DOI：

  10.1080/00397911.2021.1966038
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-hydroxy-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 生成 methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate
  参考文献：
  名称：

  SCHREINER, ERWIN;ZBIRAL, ERICH;KLEINEIDAM, REINHARD G.;SCHAUER, ROLAND, LIEBIGS ANN. CHEM.,(1991) N, C. 129-134

  摘要：

  DOI：

文献信息

• BROMOHYDROXYLATION OF GLYCALS—AN INVESTIGATION INTO THE REACTION OF SOME 4-<i>N</i>-ACYLATED DERIVATIVES OF METHYL 5-ACETAMIDO-7,8,9-TRI-<i>O</i>-ACETYL-2,6-ANHYDRO-3,4,5-TRIDEOXY-D-<i>GLYCERO</i>-D-<i>GALACTO</i>-NON-2-ENONATE AND ITS 4-EPIMER
  作者：Gaik B. Kok、Tho van Phan、Mark von Itzstein

  DOI：10.1081/car-100105710

  日期：2001.6.30

  Bromohydroxylation of some 4-N-acylated derivatives of the glycals of N-acetylneuraminic acid, methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (4) and methyl 5-aceta-mido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-talo-non-2-enonate (the 4-epimer of 4), with N-bromosuccinimide (NBS) and water in the presence of a co-solvent has provided

  N-乙酰神经氨酸，5-乙酰氨基甲基-7,8,9-三-O-乙酰基-2,6-脱水-3,4,5-三甲氧基-D的糖基的一些4-N-酰化衍生物的溴羟基化-甘油-D-半乳糖-非-2-烯酸酯（4）和5-乙酰氨基-甲基-7,8,9-三-O-乙酰基-2,6-脱水-3,4,5-三苯氧基-D在共溶剂存在下，N-溴丁二酰亚胺（NBS）和水形成的-glycero-D-talo-non-2-enonate（4的4位表位）提供了一系列新的糖基供体。发现卤代羟基化反应的立体选择性受溶剂组成，反应温度和C-4处取代基的立体电子性质的控制。
• A regio- and stereo-selective introduction of azide at C-4 of 2,3-unsaturated N-acetylneuraminic acids
  作者：Gaik B. Kok、Mark von Itzstein

  DOI：10.1016/s0008-6215(97)00124-9

  日期：1997.8

  Abstract The regio- and stereo-selective azidation of the peracetate methyl esters of 4- epi -Neu5Ac2en and 6-thio-4- epi -Neu5Ac2en has been achieved using Pd(0) chemistry in good yield (> 80%). These 4- epi -azido-4-deoxy-Neu5Ac2en derivatives provide interesting biological probes.

  摘要使用Pd（0）化学方法以良好的收率（> 80％）实现了4- epi -Neu5Ac2en和6-thio-4- epi -Neu5Ac2en过乙酸甲酯的区域选择性和立体选择性叠氮化。这些4- epi-azido-4-deoxy-Neu5Ac2en衍生物提供了有趣的生物学探针。
• Sialidase inhibitors related to zanamivir. Further SAR studies of 4-amino-4H-pyran-2-carboxylic acid-6-propylamides
  作者：Paul G Wyatt、Barry A Coomber、Derek N Evans、Torquil I Jack、Heather E Fulton、Alan J Wonacott、Peter Colman、Jose Varghese

  DOI：10.1016/s0960-894x(01)00019-1

  日期：2001.3

  SAR investigations of the 4- and 5-positions of a series of 4-amino-4H-pyran-2-carboxylic acid 6-carboxamides are reported. Potent inhibitors of influenza A sialidase with marked selectivity over the influenza B enzyme were obtained when the basic 4-amino substituent was replaced by hydroxyl or even deleted. Modifications at the 5-position exhibited a tight steric requirement, with trifluoroacetamide being optimal. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Schreiner, Erwin; Zbiral, Erich; Kleineidam, Reinhard G., Liebigs Annalen der Chemie, 1991, # 2, p. 129 - 134
  作者：Schreiner, Erwin、Zbiral, Erich、Kleineidam, Reinhard G.、Schauer, Roland

  DOI：——

  日期：——
• Synthesis of methyl 4-acetamido-N-acetyl-4-deoxy-α- and β-4-epi-neuraminic acids
  作者：B.P. Bandgar、S.V. Patil、Erich Zbiral

  DOI：10.1016/0008-6215(95)00191-u

  日期：1995.10

  Methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3,4,5-tetradeoxy-D-glycero-D-talo- nonulopyranosonate with N-bromosuccinimide in methanol gave methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-alpha-D-ralo-nonulopyranosid) and methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-beta-D-glycero-D-talo-nonulopyranosid)onate, which on reductive acetylation with H-2/Pd-C in acetic anhydride-ethyl acetate yielded the corresponding 4-acetamido analogues. Debromination with Bu(3)SnH/AIBN in toluene, followed by hydrolysis, gave methyl 4-acetamido-N-acetyl-4-deoxy-alpha-and beta-4-epi-neuraminic acids.