methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate | 59694-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl [4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside]onate；methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate；methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(4-nitrophenoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 59694-37-0
• 化学式: C₂₆H₃₂N₂O₁₅
• 分子量: 612.544
• InChiKey: IIIHVOCDPSDJTI-RLKHCHHESA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  719.5±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  225
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 在 palladium on activated charcoal 甲酸铵 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-[4-(prop-2-enoylamino)phenoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Roy, Rene; Andersson, Fredrik O.; Harms, Guenter, Angewandte Chemie, 1992, vol. 104, # 11, p. 1551 - 1554

  摘要：

  DOI：
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 123.0h， 生成 methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of poly(aspartimide)-based bio-glycoconjugates

  摘要：

  The purpose of this programme was to synthesize and analyze new bioconjugates of interest for the potential inhibition of the influenza virus, using poly(aspartimide) as a polymer support. The macromolecular targets were obtained by attaching various sialic acid-linker-amine compounds to poly(aspartimide). (1)H and (13)C NMR studies were then performed to analyze the degree of incorporation of the sialic acid-linker-amine compounds within the poly(aspartimide). These studies illustrated that the incorporation was dependent on the nature of the spacer between the sugar and the amine functionality. Thus aliphatic spacers favoured the inclusion of sialic acid onto the polymer support whereas compounds having only an aromatic moiety between the sialic acid and the amine could not be easily incorporated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.034

文献信息

• A Facile Access to Aryl <i>α</i>-Sialosides: the Combination of a Volatile Amine Base and Acetonitrile in Glycosidation of Sialosyl Chlorides
  作者：Atsuhito Kuboki、Takahiro Sekiguchi、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1055/s-1998-1717

  日期：1998.5

  We have succeeded in achieving a facile access to 4-nitrophenyl and 4-methylumbelliferyl-α-sialosides. To sialosyl chlorides which are fully protected with acetyl groups as glycosyl donors, the action of phenols with diisopropylethylamine in acetonitrile brought about high yield as well as facile product isolation.

  我们已经成功实现了对4-硝基苯基和4-甲基伞形酮-α-唾液酸苷的简易获取。对于完全被乙酰基保护的唾液酸氯化物作为糖基供体，在乙腈中使用二异丙基乙胺作用下的酚类物质带来了高产率以及简易的产品分离。
• Syntheses of C-3-Modified Sialylglycosides as Selective Inhibitors of Influenza Hemagglutinin and Neuraminidase
  作者：Xue-Long Sun、Yoshimi Kanie、Chao-Tan Guo、Osamu Kanie、Yasuo Suzuki、Chi-Huey Wong

  DOI：10.1002/1099-0690(200007)2000:14<2643::aid-ejoc2643>3.0.co;2-1

  日期：2000.7

  In an effort to develop new structures as inhibitors of both influenza virus proteins hemagglutinin and neuraminidase, a series of sialic acid derivatives, including those with one of the hydrogen atoms at the C-3 position replaced by either OH or F, were synthesized. The sialic acid derivative with a 3-eq-OH group was first synthesized by means of a new process and used as the key intermediate for

  为了开发作为流感病毒蛋白血凝素和神经氨酸酶抑制剂的新结构，合成了一系列唾液酸衍生物，包括 C-3 位置的一个氢原子被 OH 或 F 取代的那些。具有3-eq-OH基团的唾液酸衍生物首先通过新工艺合成，并作为C-3位进一步衍生化的关键中间体。研究了这些化合物在酸和唾液酸酶催化水解条件下的稳定性，结果表明这些化合物比它们的母体对硝基苯基 α-唾液酸苷对这两种条件表现出更强的抵抗力。进一步的抑制试验表明 3-ax-OH 或 F 衍生物 4、5 和 24，4 的 4-差向异构体，是来自产气荚膜梭菌的唾液酸酶的有效特异性抑制剂，以及其他测试的细菌唾液酸酶。然而，3-eq-OH 衍生物 3 几乎没有抑制作用。对人流感唾液酸酶 N1 和 N2 的抑制观察到了相同的趋势。然后将化合物 3-5 和唾液酸转化为二硬脂酰磷脂酰乙醇胺偶联物。在这些脂质体样化合物中，来自 4 和 5 的化合物对血凝素 H3 亚型显
• Efficient regeneration of the 5-acetamido group of a neuraminic acid aryl glycoside from the O-nethyl acetimidate function under acidic conditions
  作者：A. V. Orlova、A. I. Zinin、L. O. Kononov

  DOI：10.1007/s11172-010-0030-6

  日期：2009.2

  Treatment of protected N-acetylneuraminic acid 2-formyl-4-nitrophenyl glycoside with (diethyl-amino)sulfur trifluoride (DAST) and methanol resulted, apart from the known transformation of the formyl group into a difluoromethyl one, in an undocumented formation of 5-(O-methyl acetimidate) of Neu5Ac. This imidate was converted into the target 5-acetamido derivative under the action of aqueous TFA. The yield of the target product (94%) was twice as high as that reported earlier.

  使用(二乙氨基)三氟硫化物 (DAST) 和甲醇处理受保护的 N-乙酰神经氨酸 2-甲酰基-4-硝基苯基糖苷，除了已知的将甲酰基转化为二氟甲基的反应外，还导致了未记录的 Neu5Ac 的 5-(O-甲基乙酰亚胺盐)的形成。在水溶液三氟乙酸 (TFA) 的作用下，该亚胺盐被转化为目标的 5-乙酰胺衍生物。目标产物的产率 (94%) 是先前报道的产率的两倍。
• Glycosylation with ulosonates under Mitsunobu conditions: scope and limitations
  作者：Nándor Kánya、Sándor Kun、Gyula Batta、László Somsák

  DOI：10.1039/d0nj03044a

  日期：——

  A systematic study was performed by using Mitsunobu conditions (diethyl azodicarboxylate, Ph3P or n-Bu3P in THF or CH3CN) for glycosylations with methyl 3,4,5,7-tetra-O-benzoyl-α-D-gluco-hept-2-ulopyranosonate. From a set of 47 O-, N-, S- and C-nucleophiles, phenols and N-hydroxy compounds with a pKa of 5–8, phthalimide, benzotriazole, 6-chloropurine, an oxazolidinedione and several tetrazoles with

  通过使用Mitsunobu条件（在THF或CH 3 CN中的偶氮二羧酸二乙酯，Ph 3 P或n -Bu 3 P ）进行甲基，3,4,5,7-四-O-苯甲酰基-α- D的糖基化研究-葡萄糖-庚-2- ulopyranosonate。选自47种O-，N-，S-和C-亲核试剂，酚和N-羟基化合物，其ap K a为5-8，邻苯二甲酰亚胺，苯并三唑，6-氯嘌呤，恶唑烷二酮和若干具有ap K a的四唑苯酚的比例为4-8，而苯酚以中等到非常高的产率提供了相应的产物，而C-亲核试剂则没有反应性。对三卤代乙酰苯胺进行O-糖基化反应，得到O-糖基-N-芳基三卤代乙酰亚胺酸酯，这是常规的O-亚氨基化无法制备的。所有反应都是高度立体选择性的，仅产生β（D）异构体。用甲基（5-乙酰氨基-4,7,8,9-四- ø -乙酰基-3,5-二脱氧d -甘油基- d -半乳-2-壬基吡喃二酮酸）酚和苯并三唑生成了预期的产物，但
• Phase-transfer-catalyzed synthesis of aryl α-ketosides of N-acetylneuraminic acid. A 2-methylfluoran-6-yl glycoside of N-acetylneuraminic acid, 2-methyl-6-(5-acetamido-3,5-dideoxy-α-d-glycero-d-galacto-nonulopyranosyl-onic acid)xanthene-9-spiro-1′-isobenzofuran-3′-one, a new substrate for neuraminidase assay
  作者：Jörg Rothermel、Hans Faillard

  DOI：10.1016/0008-6215(90)84104-3

  日期：1990.2

  catalysis in chloroform-aqueous alkali gave several known and some new aryl alpha-ketosides in a short reaction time and in good yields. The 4-methylumbelliferyl alpha-ketoside, the standard substrate for neuraminidase, was prepared in a yield of up to 70%. New Neu5Ac ketosides were prepared with fluorescein and the fluorescein analog, 2-methyl-6-hydroxyfluoran (2-methyl-6-hydroxyxanthene-9-spiro-1'-isobenzofuran-3'-one)

  通过在氯仿-水溶液中的相转移催化对N-乙酰神经氨酸进行糖苷化反应，可以在较短的反应时间内以高收率得到几种已知的和一些新的芳基α-酮苷。制备了神经氨酸酶的标准底物4-甲基伞形酮基α-酮基，产率最高为70％。用荧光素和荧光素类似物2-甲基-6-羟基荧烷（2-甲基-6-羟基氧杂蒽-9-螺基-1'-异苯并呋喃-3'-one）作为糖苷配基制备了新的Neu5Ac酮苷。 2-（2-羟基-5-甲基-苯甲酰基）苯甲酸和3-氟苯酚。α构型通过400-MHz 1H-nmr光谱法和通过用霍乱弧菌和产气荚膜梭菌的神经氨酸酶裂解酮苷来确定。