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N-acetyl neuraminic acid | 19342-33-7

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

N-acetyl neuraminic acid

英文别名

sialic acid；Neu5Ac；N-acetyl-D-neuraminic acid；β-Neu5Ac；NANA；(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid；β-N-acetyl-neuraminic acid；5-N-acetylneuraminic acid；lactaminic acid；NeuAc；β-sialic acid；UX-001 SA-ER；N-acetyl-beta-neuraminic acid；(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

CAS

19342-33-7

化学式

C₁₁H₁₉NO₉

mdl

——

分子量

309.273

InChiKey

SQVRNKJHWKZAKO-PFQGKNLYSA-N

BEILSTEIN

——

EINECS

——

物化性质

物理描述：

Solid
熔点：

186°C
碰撞截面：

166.6 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

辛醇/水分配系数(LogP)：

-3.5
重原子数：

21
可旋转键数：

5
环数：

1.0
sp3杂化的碳原子比例：

0.82
拓扑面积：

177
氢给体数：

7
氢受体数：

9

SDS

SDS：58e4e04536b4e898e2256b074f0340a8

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
N-乙酰神经氨酸水合物	sialic acid	21646-00-4	C₁₁H₁₉NO₉	309.273
N-乙酰神经氨酸甲酯	N-acetylneuraminic acid methyl ester	22900-11-4	C₁₂H₂₁NO₉	323.3
——	methyl 6-O-(5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosylonic acid)-α-D-glucopyranoside	——	C₁₈H₃₁NO₁₄	485.442
——	3'-sialyllactose	——	C₂₃H₃₉NO₁₉	633.558
——	N-acetyl-β-neuraminic acid 1,7-lactone	335592-15-9	C₁₁H₁₇NO₈	291.258
——	methyl 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate	270563-79-6	C₁₉H₂₅NO₁₀	427.408
——	N-acetyl-D-mannosamine	7772-94-3	C₈H₁₅NO₆	221.21
——	N-acetyl-D-mannosamine	14131-64-7	C₈H₁₅NO₆	221.21
——	D-GlcNAc	7512-17-6	C₈H₁₅NO₆	221.21

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	b-NeuAc4Me	68355-09-9	C₁₂H₂₁NO₉	323.3
——	9-O-acetyl-N-acetylneuraminic acid	81228-99-1	C₁₃H₂₁NO₁₀	351.31
——	5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-galactononulopyranosonate	114857-71-5	C₁₄H₂₃NO₉	349.338
N-乙酰神经氨酸甲酯	N-acetylneuraminic acid methyl ester	22900-11-4	C₁₂H₂₁NO₉	323.3
——	methyl sialate	——	C₁₂H₂₁NO₉	323.3
——	N-Acetylneuraminic acid methyl ester	50998-13-5	C₁₂H₂₁NO₉	323.3
——	methyl N-acetyl-β-neuraminoside	23755-35-3	C₁₂H₂₁NO₉	323.3
——	N-([(2)H3]-acetyl)-β-neuraminic acid	1312777-24-4	C₁₁H₁₉NO₉	312.249
——	alpha-Neup5Ac-(2->8)-beta-Neup5Ac	131696-33-8	C₂₂H₃₆N₂O₁₇	600.531
——	4-O-acetyl-N-acetylneuraminic acid	55600-96-9	C₁₃H₂₁NO₁₀	351.31
5-乙酰氨基-3,5-二脱氧-6-(1,2,3-三羟基丙基)己-2-酮吡喃糖苷酸二甲基酯	N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid	6730-43-4	C₁₃H₂₃NO₉	337.327
——	N-([(2)H2]-glycolyl)-β-neuraminic acid	1312777-29-9	C₁₁H₁₉NO₁₀	327.257
——	2-O-methyl-5-N-glycolylmethyl-β-neuraminate	31143-38-1	C₁₃H₂₃NO₁₀	353.326
——	Methyl-5-(acetylamino)-3,5-dideoxy-8,9-O-isopropyliden-β-D-glycero-D-galacto-2-nonulopyranosidonsaeure-methylester	88481-35-0	C₁₆H₂₇NO₉	377.392
——	5-acetamido-7-O-acetyl-3,5-dideoxy-D-glycero-D-galactononulopyranosic acid	521-77-7	C₁₃H₂₁NO₁₀	351.31
——	3'-sialyllactose	——	C₂₃H₃₉NO₁₉	633.558
——	O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonicacid)-(2→3)-O-(β-D-galactopyranosyl)-(1→4)-O-(β-D-glucopyranosyl)octanol	——	C₃₁H₅₅NO₁₉	745.773
——	methyl (methyl 5-acetamido-3,4,5-trideoxy-4-methoxy-8,9-O-isopropylidene-D-glycero-β-D-galacto-2-nonulopyranosid)onate	177898-31-6	C₁₇H₂₉NO₉	391.419
——	Neu5Acα(2-3)Galβ(1-3)GalNAc	——	C₂₅H₄₂N₂O₁₉	674.61
——	5-acetamido-2-O-acetyl-3,5-dideoxy-D-glycero-D-galactononulopyranosic acid	——	C₁₃H₂₁NO₁₀	351.31
——	N-acetyl-β-neuraminic acid 1,7-lactone	335592-15-9	C₁₁H₁₇NO₈	291.258
——	N-([(2)H3]-acetyl)-2-O-methyl-β-neuraminic acid methyl ester	1312776-87-6	C₁₃H₂₃NO₉	340.303
——	(2S,4S,5R,6R)-benzyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-1-carboxylate	113757-75-8	C₁₈H₂₅NO₉	399.398
4,7,8,9-四-O-乙酰基-N-乙酰神经氨酸甲酯	4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester	84380-10-9	C₂₀H₂₉NO₁₃	491.449
——	N-([(2)H2]-glycolyl)-2-O-methyl-β-neuraminic acid methyl ester	1312776-95-6	C₁₃H₂₃NO₁₀	355.31
——	N-([(2)H3]-acetyl)-β-neuraminic acid 1,7-lactone	1312777-36-8	C₁₁H₁₇NO₈	294.234
——	methyl (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-3-[(2S)-2-amino-3-phenylpropanoyl]oxy-1,2-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylate	771577-92-5	C₂₁H₃₀N₂O₁₀	470.477
——	N-([(2)H2]-glycolyl)-β-neuraminic acid 1,7-lactone	1312777-43-7	C₁₁H₁₇NO₉	309.241
——	2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure	19342-36-0	C₂₁H₂₉NO₁₄	519.46
——	5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-4-O-tert-butyldimethylsilyl-D-glycero-D-galacto-nonulopyranosic acid	1354483-47-8	C₂₀H₃₇NO₉Si	463.601
——	5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galactononulopyranosic acid	1354483-43-4	C₁₈H₂₃NO₉	397.382
——	methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate	1354483-42-3	C₁₉H₂₅NO₉	411.409
——	azido O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside	——	C₂₃H₃₈N₄O₁₈	658.571
2-O-甲基beta-神经氨酸甲基酯	methyl (methyl 5-amino-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate	56070-37-2	C₁₁H₂₁NO₈	295.29
——	methyl (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxypropyl]-2,4-dihydroxyoxane-2-carboxylate	771577-91-4	C₂₆H₃₈N₂O₁₂	570.594
——	2-benzyloxycarbonyl-N-acetyl-β-neuraminic acid 1,7-lactone	1095319-92-8	C₁₉H₂₃NO₁₀	425.392
——	N-([(2)H3]-acetyl)-3,3-[(2)H2]-β-neuraminic acid	1312777-26-6	C₁₁H₁₉NO₉	314.233
——	N-([(2)H2]-glycolyl)-3,3-[(2)H2]-β-neuraminic acid	1312777-32-4	C₁₁H₁₉NO₁₀	329.241
——	5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-2-O-triethylsilyl-4-O-tert-butyldimethylsilyl-D-glycero-D-galacto-nonulopyranosic acid	1354483-51-4	C₂₆H₅₁NO₉Si₂	577.863
——	2-benzyloxycarbonyl-N-([(2)H3]-acetyl)-β-neuraminic acid 1,7-lactone	1312777-08-4	C₁₉H₂₃NO₁₀	428.369
——	5-acetamido-4-O-tert-butyldimethylsilyl-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosic acid	1354483-45-6	C₂₄H₃₇NO₉Si	511.645
——	2-benzyloxycarbonyl-N-([(2)H2]-glycolyl)-β-neuraminic acid 1,7-lactone	1312777-14-2	C₁₉H₂₃NO₁₁	443.376
——	N-acetyl-D-mannosamine	7772-94-3	C₈H₁₅NO₆	221.21
——	methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-(1-hydroxypentyl)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	771577-95-8	C₁₇H₃₁NO₉	393.434
——	3,3-[(2)H2]-N-([(2)H3]-acetyl)-β-neuraminic acid 1,7-lactone	1312777-40-4	C₁₁H₁₇NO₈	296.218
——	benzyl 5-acetamido-3,5-dideoxy-2,4,7,8,9-penta-O-trimethylsilyl-D-glycero-D-galactononulpyranosonate	——	C₃₃H₆₅NO₉Si₅	760.308
——	N-([(2)H2]-glycolyl)-3,3-[(2)H2]-β-neuraminic acid 1,7-lactone	1312777-46-0	C₁₁H₁₇NO₉	311.226
——	[(2R)-2-[(1R,2S,5R,7S,8R)-8-(2,2,3,3,4,4,4-heptafluorobutanoylamino)-5,7-bis(2,2,3,3,4,4,4-heptafluorobutanoyloxy)-4-oxo-3,9-dioxabicyclo[3.3.1]nonan-2-yl]-2-(2,2,3,3,4,4,4-heptafluorobutanoyloxy)ethyl] 2,2,3,3,4,4,4-heptafluorobutanoate	1243249-86-6	C₂₉H₁₀F₃₅NO₁₂	1229.34
——	N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester	67670-69-3	C₂₀H₂₈ClNO₁₂	509.895
甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯	methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate	116450-06-7	C₂₁H₃₁NO₁₂S	521.543
——	5-acetamido-2,6-anhydro-3,5-dideoxy-4-O-methyl-D-glycero-D-galacto-non-2-enonic acid	——	C₁₂H₁₉NO₈	305.285
——	2-benzyloxycarbonyl-3,3-[(2)H2]-N-([(2)H3]-acetyl)-β-neuraminic acid 1,7-lactone	1312777-11-9	C₁₉H₂₃NO₁₀	430.353
——	methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-(2-hydroxy-1,3-diphenylpropan-2-yl)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	771577-93-6	C₂₇H₃₅NO₉	517.576
——	2-benzyloxycarbonyl-N-([(2)H2]-glycolyl)-3,3-[(2)H2]-β-neuraminic acid 1,7-lactone	1312777-17-5	C₁₉H₂₃NO₁₁	445.36
——	(2S,4S,5R,6R)-5-acetamido-N-[[(2R,3S,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxamide	1338344-44-7	C₂₀H₃₀N₄O₁₃	534.477
——	(2S)-2-[[(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carbonyl]amino]-4-methylpentanoic acid	1421960-08-8	C₁₇H₂₈N₂O₉	404.417
——	(2S)-2-[[(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carbonyl]amino]-3-methylbutanoic acid	1421960-10-2	C₁₆H₂₆N₂O₉	390.39
——	N-[(2R,3R,4S)-4-hydroxy-6-(morpholine-4-carbonyl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-3-yl]acetamide	1421960-12-4	C₁₅H₂₄N₂O₈	360.364
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
——	(2R,3R,4S)-3-acetamido-N-benzyl-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxamide	1421960-13-5	C₁₈H₂₄N₂O₇	380.398
(4S,5R,6R)-5-乙酰氨基-4-氨基-6-((1R,2R)-2,3-二羟基-1-甲氧基丙基)-5,6-二氢-4H-吡喃-2-羧酸	(2R,3R,4S)-3-acetamide-4-amino-2-[(1R,2R)-2,3-dihydroxy-1-methoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid	475483-21-7	C₁₂H₂₀N₂O₇	304.3
——	cytidine-5'-monophosphono-N-acetylneuraminic acid	3063-71-6	C₂₀H₃₁N₄O₁₆P	614.457
——	CMP-Neu5Ac	126253-08-5	C₂₀H₃₁N₄O₁₆P	614.457
——	D-glycero-D-galacto-Non-2-enonamide, 5-(acetylamino)-2,6-anhydro-3,5-dideoxy-N-[(4-methoxyphenyl)methyl]-	1421960-07-7	C₁₉H₂₆N₂O₈	410.424
扎那米韦	zanamivir	139110-80-8	C₁₂H₂₀N₄O₇	332.313
——	(2S)-2-[[(2R,3R,4S)-3-acetamido-4-amino-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carbonyl]amino]-3-methylbutanoic acid	1421960-14-6	C₁₆H₂₇N₃O₈	389.406
——	(2S)-2-[[(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carbonyl]amino]-2-phenylacetic acid	1421960-11-3	C₁₉H₂₄N₂O₉	424.408

反应信息

作为反应物：

描述：

N-acetyl neuraminic acid 在 ammonium hydroxide 作用下，以水为溶剂，以430.8 g的产率得到ammonium N-acetylneuraminate

参考文献：

名称：

CRYSTAL OF AMMONIUM N-ACETYLNEURAMINATE ANHYDRATE, AND PROCESS FOR PRODUCING SAME

摘要：

根据本发明，提供了一种无水铵N-乙酰神经酸盐晶体，以及一种生产无水铵N-乙酰神经酸盐晶体的方法，包括向含有铵盐化合物的N-乙酰神经酸水溶液中滴加或逐滴加入从醇类和酮类中选择的溶剂，使铵N-乙酰神经酸盐晶体沉淀，然后从水溶液中收集铵N-乙酰神经酸盐晶体。

公开号：

US20180002364A1
作为产物：

描述：

在 palladium dihydroxide 盐酸、 4-二甲氨基吡啶、 ruthenium trichloride 、 sodium periodate 、水、氢气、碳酸氢钠、 potassium carbonate 、臭氧、盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺作用下，以甲醇、四氯化碳、乙醇、二氯甲烷、水、乙腈为溶剂，生成 N-acetyl neuraminic acid

参考文献：

名称：

N-乙酰神经氨酸的不对称合成

摘要：

N-乙酰神经氨酸1的高度非对映选择性合成已经通过顺式烯烃6和反式烯烃10分别通过分子内苯基硒酰胺化和锇酰化的立体选择性功能化来完成。

DOI：

10.1039/a909400h

点击查看最新优质反应信息

文献信息

[EN] DERIVATIVES OF AMANITA TOXINS AND THEIR CONJUGATION TO A CELL BINDING MOLECULE<br/>[FR] DÉRIVÉS DE TOXINES D'AMANITES ET LEUR CONJUGAISON À UNE MOLÉCULE DE LIAISON CELLULAIRE

申请人：HANGZHOU DAC BIOTECH CO LTD

公开号：WO2017046658A1

公开（公告）日：2017-03-23

Derivatives of Amernita toxins of Formula (I), wherein, formula (a) R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, X, L, m, n and Q are defined herein. The preparation of the derivatives. The therapeutic use of the derivatives in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

Amernita毒素的衍生物的化学式（I），其中，化学式（a）中的R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10、X、L、m、n和Q在此处被定义。这些衍生物的制备。这些衍生物在靶向治疗癌症、自身免疫性疾病和传染病中的治疗用途。
[EN] A CONJUGATE OF A CYTOTOXIC AGENT TO A CELL BINDING MOLECULE WITH BRANCHED LINKERS<br/>[FR] CONJUGUÉ D'UN AGENT CYTOTOXIQUE À UNE MOLÉCULE DE LIAISON CELLULAIRE AVEC DES LIEURS RAMIFIÉS

申请人：HANGZHOU DAC BIOTECH CO LTD

公开号：WO2020257998A1

公开（公告）日：2020-12-30

Provided is a conjugation of cytotoxic drug to a cell-binding molecule with a side-chain linker. It provides side-chain linkage methods of making a conjugate of a cytotoxic molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and immunological disorders.

提供了一种将细胞毒性药物与一个侧链连接分子结合的共轭物。它提供了制备细胞毒性分子与细胞结合配体的共轭物的侧链连接方法，以及在靶向治疗癌症、感染和免疫性疾病中使用该共轭物的方法。
[EN] CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES<br/>[FR] DÉRIVÉ DE DIMÈRE DE PYRROLOBENZODIAZÉPINE RÉTICULÉ (PBD) ET SES CONJUGUÉS

申请人：HANGZHOU DAC BIOTECH CO LTD

公开号：WO2020006722A1

公开（公告）日：2020-01-09

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

一种新型的交联细胞毒剂，吡咯苯并二氮杂环二聚体（PBD）衍生物，以及它们与细胞结合分子的结合物，一种制备这些结合物的方法以及这些结合物的治疗用途。
ANTI-EGFR ANTIBODY DRUG CONJUGATES

申请人：AbbVie Inc.

公开号：US20190153107A1

公开（公告）日：2019-05-23

The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.

这项发明涉及抑制Bcl-xL的抗表皮生长因子受体（EGFR）抗体药物结合物（ADCs），包括使用所述ADCs的组合物和方法。
[EN] 6H-THIENO`2, 3-B!PYRROLE DERIVATIVES AS ANTAGONISTS OF GONADOTROPIN RELEASING HORMONE (GNRH)<br/>[FR] DERIVES DE 6H-THIENO`2,3-B!PYRROLE EN TANT QU'ANTAGONISTES DE LA GONADOLIBERINE (GNRH)

申请人：ASTRAZENECA AB

公开号：WO2004018480A1

公开（公告）日：2004-03-04

The invention relates to a group of novel thieno-pyrrole compounds of Formula (I): wherein: R1, R2, R3, R4 and R5 are as defined in the specification, which are useful as gonadotrophin releasing hormone antagonists. The invention also relates to pharmaceutical formulations of said compounds, methods of treatment using said compounds and to processes for the preparation of said compounds.

这项发明涉及一组新型噻吩-吡咯烷化合物的化学式（I）：其中：R1、R2、R3、R4和R5如规范中定义，这些化合物可用作促性腺激素释放激素拮抗剂。该发明还涉及所述化合物的药物配方、使用所述化合物的治疗方法以及所述化合物的制备方法。