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methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid | 152178-79-5

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

中文名称

——

中文别名

——

英文名称

methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

英文别名

5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester；methyl 5-acetamido-4-azido-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosoate；Zanamivir Azide Methyl Ester；methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate

methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid化学式

CAS

152178-79-5

化学式

C₁₂H₁₈N₄O₇

mdl

——

分子量

330.298

InChiKey

MMLUEZXBKJUPII-CNYIRLTGSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

160-162°C
溶解度：

DMSO（微溶）、甲醇（微溶）、水（微溶）

计算性质

辛醇/水分配系数(LogP)：

-0.4
重原子数：

23
可旋转键数：

7
环数：

1.0
sp3杂化的碳原子比例：

0.67
拓扑面积：

140
氢给体数：

4
氢受体数：

9

SDS

SDS：c4c53d62e5f08f1b06f54caf72f31cb9

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
甲基(3aR,4R,7aR)-2-甲基-4-[(1S,2R)-1,2,3-三乙酰氧基丙基]-3a,7a-二氢-4H-吡喃并[3,4-d][1,3]恶唑-6-羧酸酯	methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate	78850-37-0	C₁₈H₂₃NO₁₀	413.381

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(4S,5R,6R)-5-acetylamino-4-azido-6-[(S)-hydroxy-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	188529-20-6	C₁₃H₁₆N₄O₈	356.292
——	methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-8,9-O-isopropylidene-D-glycero-D-galacto-non-2-enonic acid	203119-18-0	C₁₅H₂₂N₄O₇	370.362
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(S)-[(4R)-2-oxo-1,3-dioxolan-4-yl]-(propylcarbamoyloxy)methyl]-3,4-dihydro-2H-pyran-6-carboxylate	1053413-05-0	C₁₇H₂₃N₅O₉	441.398
——	(4S,5R,6R)-5-acetylamino-4-azido-6-[(S)-heptylcarbamoyloxy-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	188529-21-7	C₂₁H₃₁N₅O₉	497.505
——	(4S,5R,6R)-5-acetylamino-4-azido-6-[(S)-(2-hydroxyethylcarbamoyloxy)-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	252061-42-0	C₁₆H₂₁N₅O₁₀	443.37
——	(4S,5R,6R)-5-acetylamino-4-azido-6-{(S)-(2-oxo-[1,3]dioxolan-4R-yl)-[(6-tert-butoxycarbonylamino-hexyl)-carbamoyloxy]-methyl}-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	188529-35-3	C₂₅H₃₈N₆O₁₁	598.61
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(S)-2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butylamino]ethylcarbamoyloxy-[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl]-3,4-dihydro-2H-pyran-6-carboxylate	1053691-41-0	C₂₅H₃₉N₇O₁₁	613.625
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(S)-dipropylcarbamoyloxy-[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl]-3,4-dihydro-2H-pyran-6-carboxylate	1053640-39-3	C₂₀H₂₉N₅O₉	483.478
扎那米韦中间体2	5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid	130525-62-1	C₁₁H₁₈N₂O₇	290.273
——	(4S,5R,6R)-5-acetylamino-4-azido-6-[(S)-(4-nitrophenoxycarbonyloxy)-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	188529-34-2	C₂₀H₁₉N₅O₁₂	521.397
——	(2R,3R,4S)-3-acetamido-4-amino-2-[(1R,2R)-1-(heptylcarbamoyloxy)-2,3-dihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid	188529-22-8	C₁₉H₃₃N₃O₈	431.486
——	(2R,3R,4S)-3-Acetylamino-4-azido-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-methyl ester	204197-14-8	C₁₀H₁₂N₄O₆	284.228
——	[(S)-[(2R,3R,4S)-3-acetamido-4-azido-6-methoxycarbonyl-3,4-dihydro-2H-pyran-2-yl]-[(4R)-2-oxo-1,3-dioxolan-4-yl]methyl] 4-(2-phenylacetyl)piperazine-1-carboxylate	1054665-48-3	C₂₆H₃₀N₆O₁₀	586.558
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-(propylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylate	204197-16-0	C₁₃H₁₉N₅O₅	325.324
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-(2-hydroxyethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylate	1054613-14-7	C₁₂H₁₇N₅O₆	327.297
——	methyl (2R,3R,4S)-3-acetamido-4-azido-2-(dimethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylate	204197-18-2	C₁₂H₁₇N₅O₅	311.297
——	(2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(1R,2R)-1-(heptylcarbamoyloxy)-2,3-dihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid	1054814-87-7	C₃₀H₅₁N₅O₁₂	673.761
——	(4S,5R,6R)-5-acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-6-[(S)-[(2-hydroxyethyl)-carbamoyloxy]-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	252061-43-1	C₂₇H₄₁N₅O₁₄	659.648
——	(4S,5R,6R)-5-acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-6-[(S)-[(2-bromoethyl)-carbamoyloxy]-(2-oxo-[1,3]dioxolan-4R-yl)-methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	252061-44-2	C₂₇H₄₀BrN₅O₁₃	722.544
——	methyl (2R,3R,4S)-3-acetamido-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-[(1R,2R)-2,3-dihydroxy-1-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylcarbamoyloxy]propyl]-3,4-dihydro-2H-pyran-6-carboxylate	252061-49-7	C₃₂H₅₃N₅O₁₈	795.796
——	5-acetamido-4-azido-2,6-anhydro-3,4,5-trideoxy-6-(((benzyloxy)amino)methyl)-L-gluco-hex-2-enonic acid	1428441-26-2	C₁₆H₁₉N₅O₅	361.357
——	5-acetamido-4-azido-2,6-anhydro-3,4,5-trideoxy-6-((phenylamino)methyl)-L-gluco-hex-2-enonic acid	1428441-17-1	C₁₅H₁₇N₅O₄	331.331
——	(2R,3R,4S)-3-Acetylamino-4-azido-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-methyl ester 2-pentafluorophenyl ester	204197-15-9	C₁₆H₁₁F₅N₄O₆	450.279
——	5-acetamido-4-azido-2,6-anhydro-3,4,5-trideoxy-6-((2-phenylhydrazinyl)methyl)-L-gluco-hex-2-enonic acid	1428441-33-1	C₁₅H₁₈N₆O₄	346.346
——	5-acetamido-4-azido-2,6-anhydro-3,4,5-trideoxy-6-(([1,1′-biphenyl]-4-ylamino)methyl)-L-gluco-hex-2-enonic acid	1428441-20-6	C₂₁H₂₁N₅O₄	407.429
——	5-acetylamino-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-6-[((2,2-dimethyl-[1,3]dioxolan-4-yl)-(4-nitrophenoxy)carbonyloxy)methyl]-5,6-dihydro-4H-pyran-2-carboxylic acid ethyl ester	——	C₃₃H₄₅N₅O₁₅	751.745
——	5-acetamido-4-azido-2,6-anhydro-3,4,5-trideoxy-6-((benzyl(benzyloxy)amino)methyl)-L-gluco-hex-2-enonic acid	1428441-30-8	C₂₃H₂₅N₅O₅	451.482
——	(2R,3R,4S)-3-acetamido-4-amino-2-(propylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid	——	C₁₂H₁₉N₃O₅	285.3
——	(2R,3R,4S)-3-acetamido-4-amino-2-(2-hydroxyethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid	——	C₁₁H₁₇N₃O₆	287.272
——	(2R,3R,4S)-3-acetamido-4-amino-2-(2-aminoethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid	204196-85-0	C₁₁H₁₈N₄O₅	286.288
——	(2R,3R,4S)-3-acetamido-4-amino-2-(carboxymethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid	——	C₁₁H₁₅N₃O₇	301.256
——	(2R,3R,4S)-3-acetamido-4-amino-2-(dimethylcarbamoyl)-3,4-dihydro-2H-pyran-6-carboxylic acid	——	C₁₁H₁₇N₃O₅	271.273
——	5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-6-((phenylamino)methyl)-L-gluco-hex-2-enonic acid	1428441-18-2	C₁₅H₁₉N₃O₄	305.334
——	(5R)-acetylamino-(4S)-[4-[(3β-hydroxylup-20(29)-en-28-oyl)amino]methyl-1,2,3-triazol-1-yl]-(6R)-((1R,2R)-1,2,3-trihydroxypropyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester	——	C₄₅H₆₉N₅O₉	824.071

反应信息

作为反应物：

描述：

methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid 在吡啶、 sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、环己烯作用下，以四氢呋喃、甲醇、 N,N-二甲基甲酰胺、叔丁醇为溶剂，反应 31.5h，生成

参考文献：

名称：

Smith, Paul W.; Sollis, Steven L.; Howes, Peter D., Journal of Medicinal Chemistry, 1998, vol. 41, # 6, p. 787 - 797

摘要：

DOI：
作为产物：

描述：

N-乙酰神经氨酸水合物在吡啶、甲醇、 4-二甲氨基吡啶、三氟甲磺酸三甲基硅酯、叠氮基三甲基硅烷、 sodium methylate 作用下，以乙酸乙酯、叔丁醇为溶剂，反应 3.0h，生成 methyl 5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid

参考文献：

名称：

新型五环三萜-Neu5Ac2en衍生物的合成及其体外抗流感活性的研究

摘要：

唾液酸（Neu5Ac）衍生物，类似物及其结合物是重要的药效团。唾液酸C-4的修饰可产生具有强大抗流感活性的衍生物，例如扎那米韦。在这里，我们描述了通过与天然衍生的五环三萜（中药的一种活性成分）结合来合成新型C-4修饰的唾液酸衍生物，以及对其体外抗流感A / WSN / 33（H1N1）病毒的评估MDCK细胞中的进入活性。有趣的是，在Zemplén条件下，两种五环三萜-唾液酸共轭物的脱O-乙酰化反应过程中获得了一组构型异构体，并提出了一种机理。由于Neu5Ac2en部分的附着，所有合成的缀合物均显示出比其母体化合物更低的疏水性（AlogP）。与乌苏烷和戊烷型五环三萜烯相比，齐墩果烷型五环三萜官能化的Neu5Ac2en共轭物最有前途，并且与参考化合物姜黄素（一种针对流感血凝素的小分子进入抑制剂）相比，具有更高的活性和选择性。在酰胺键和Neu5Ac2en之间插入（1,2,3-三唑-4-基）甲基会

DOI：

10.1039/c7md00245a

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文献信息

Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) modified in the glycerol side-chain

作者：David M Andrews、Peter C Cherry、David C Humber、Paul S Jones、Steven P Keeling、Paul F Martin、Caroline D Shaw、Stephen Swanson

DOI：10.1016/s0223-5234(00)80026-4

日期：1999.7

Analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) have been prepared containing carbamate substituents at the 7-hydroxy position. (4S,5R,6R)-5-Acetylamino-6-[1R-[(6-aminohexyl)carbamoyloxy]-2R,3-dihydroxypropyl]-4-guanidino-5,6-dihydro-4H-pyran-2carboxylic acid and (4S,5R,6R)-5-Acetylamino-6-[1R-[heptylcarbamoyloxy]-2R,3-dihydroxypropyl]-4-guanidino-5,6-dihydro4H-pyran2-carboxylic acid were the two analogues

已经制备了4-胍基-Neu5Ac2en（扎那米韦）的类似物，其在7-羟基位置含有氨基甲酸酯取代基。（4S，5R，6R）-5-乙酰氨基-6- [1R-[（6-氨基己基）氨基甲酰氧基] -2R，3-二羟丙基] -4-胍基-5，6-二氢-4H-吡喃-2羧酸和（4S，5R，6R）-5-乙酰氨基-6- [1R- [庚基氨基甲酰氧基] -2R，3-二羟丙基] -4-胍基-5,6-二氢4H-吡喃2-羧酸是具有可比的活性的两个类似物扎那米韦，在体外对流感病毒唾液酸酶具有有效的抑制作用，并具有良好的抗病毒活性。
Neuraminic acid derivatives, their preparation and their medical use

申请人：Sankyo Company, Limited

公开号：US06340702B1

公开（公告）日：2002-01-22

Compounds of formula (I) or their salts or esters: have excellent sialidase inhibitory activity and are therefore useful for the treatment and prevention of influenza and other viral diseases where the replication of the virus is susceptible to sialidase inhibitors.

化合物的结构式(I)或其盐或酯：具有出色的唾液酸酶抑制活性，因此可用于治疗和预防流感和其他病毒性疾病，其中病毒的复制易受唾液酸酶抑制剂的影响。
Regioselective synthesis of 4azido-Neu2en5,7Ac21Me and its intramolecular transformation to 4azido-Neu2en5,9Ac21Me

作者：Qingjie Zhao、Yuanyuan Lou、Ruisheng Xiong、Haihong Li、Jingshan Shen

DOI：10.1016/j.carres.2008.06.016

日期：2008.9

Methyl 5-N-acetyl-7-O-acetyl-4-azido-2,3-didehydro-2,4-dideoxy-neuraminic acid (4azido-Neu2en5,7 Ac(2)1Me) was synthesized regioselectively starting from 4azido-Neu2en5Ac1Me in high yield. The transformation of 4azido-Neu2en5,7Ac(2)1Me to the corresponding thermodynamically stable 4azido-Neu2en5,9Ac(2)1Me via intramolecular acetyl migration was confirmed by single-crystal X-ray diffraction analysis

甲基5-N-乙酰基-7-O-乙酰基-4-叠氮基2,3-didehydro-2,4-dideoxy-神经氨酸（4azido-Neu2en5,7 Ac（2）1Me）从4azido- Neu2en5Ac1Me高产量。通过单晶X射线衍射分析证实了4azido-Neu2en5,7Ac（2）1Me通过分子内乙酰基迁移到相应的热力学稳定的4azido-Neu2en5,9Ac（2）1Me的转化。讨论了建议的重排机制。
Chandler, Malcolm; Bamford, Mark J.; Conroy, Richard, Journal of the Chemical Society. Perkin transactions I, 1995, # 9, p. 1173 - 1180

作者：Chandler, Malcolm、Bamford, Mark J.、Conroy, Richard、Lamont, Brian、Patel, Bina、et al.

DOI：——

日期：——
WO2020051498A5

申请人：——

公开号：WO2020051498A5

公开（公告）日：2022-09-13