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二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯 | 144240-36-8

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

二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯

中文别名

——

英文名称

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

英文别名

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosidonate)；methyl(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate；methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-methylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate

二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯化学式

CAS

144240-36-8

化学式

C₂₁H₃₁NO₁₂S

mdl

——

分子量

521.543

InChiKey

VUDPJAWMOISBAC-KUHALTKMSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

1
重原子数：

35
可旋转键数：

15
环数：

1.0
sp3杂化的碳原子比例：

0.71
拓扑面积：

195
氢给体数：

1
氢受体数：

13

安全信息

危险品标志：

T
安全说明：

S23,S26,S36/37/39,S45,S53
危险类别码：

R23/24/25,R45,R36/37/38,R46

SDS

SDS：aea0b146b6896d3cc735e56ad81e55fd

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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-acetylneuraminic acid methyl ester	——	C₁₂H₂₁NO₉	323.3
——	N-acetyl neuraminic acid	131-48-6	C₁₁H₁₉NO₉	309.273

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid	153718-25-3	C₂₀H₂₉NO₁₂S	507.516
——	Methyl [methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranosid]onate	207910-42-7	C₂₃H₃₃NO₁₃S	563.58
——	methyl (4S,5R,6R)-4-acetyloxy-2-methylsulfanyl-5-[(2-phenylmethoxyacetyl)amino]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate	195434-88-9	C₂₈H₃₇NO₁₃S	627.667
——	methyl (methyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate	130333-20-9	C₁₃H₂₃NO₈S	353.394
——	methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate	374573-36-1	C₁₉H₂₇N₃O₁₁S	505.503
——	methyl (methyl 4,7,8,9-tetra-O-acetyl-5-azido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranosid)onate	374573-66-7	C₁₉H₂₇N₃O₁₁S	505.503
——	(4S,5R,6R)-5-Amino-4-hydroxy-2-methylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester	195434-85-6	C₁₁H₂₁NO₇S	311.356
——	methyl (2S,4S,5R,6R)-4-acetyloxy-5-(diacetylamino)-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(benzoyloxymethyl)-6-methylsulfanyloxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate	207910-45-0	C₄₀H₅₁NO₂₁S	913.905
——	(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester	256639-65-3	C₆₉H₉₅NO₂₁	1274.51
——	(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester	256639-64-2	C₆₉H₉₅NO₂₁	1274.51
——	2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-benzoyl-β-D-galactopyranoside	121377-30-8	C₃₈H₅₅NO₁₉Si	857.936
——	2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-3-O-benzoyl-β-D-galactopyranoside	121377-28-4	C₃₈H₅₅NO₁₉Si	857.936
——	methyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate	19342-75-7	C₂₇H₃₅NO₁₃	581.574
——	methyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate	19342-74-6	C₂₇H₃₅NO₁₃	581.574
——	O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3-di-O-acetyl-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol	153373-58-1	C₃₈H₅₀N₂O₂₀	854.816
——	O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3,4-tri-O-acetyl-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-galactitol	153482-74-7	C₄₀H₅₂N₂O₂₁	896.854
——	2-(Trimethylsilyl)ethyl 6-O-benzoyl-3-O-[methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate]-β-D-galactopyranoside	207910-43-8	C₄₀H₅₇NO₂₀Si	899.973
——	2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-onate>-β-D-galactopyranosyl>-β-D-glucopyranoside	156727-01-4	C₇₉H₉₇NO₂₃Si	1456.72
——	2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-onate>-β-D-galactopyranosyl>-β-D-glucopyranoside	156727-02-5	C₇₉H₉₇NO₂₃Si	1456.72
——	2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-[(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosynate)]-(2->6)-β-D-galactopyranoside	702676-48-0	C₆₅H₇₇NO₂₇Si	1332.4
——	methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3,5-dihydroxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate	246865-86-1	C₄₁H₆₃NO₁₈Si	886.033
——	4-methoxyphenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-α-D-galacto-2-nonoulopyranosylonate)-(2->3)-[(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->6)]-(β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside	1172114-36-1	C₈₇H₁₀₁NO₂₉	1624.75
——	methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate	73960-72-2	C₂₀H₂₇NO₁₂	473.434
——	5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside	190269-56-8	C₇₃H₈₅N₅O₂₄	1416.5
——	octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1c->4b-lactone)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside	446277-28-7	C₆₆H₈₃NO₁₈	1178.38
——	N-[(2S,2'R,3'R,4'S,4aR,5S,7R,8R,8aR)-7-[(2R,3S,4R,5R,6R)-5-acetamido-6-(6-azidohexoxy)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-(fluoromethyl)-4',8-dihydroxy-3-oxo-2'-[(1R,2R)-1,2,3-trihydroxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,6'-oxane]-3'-yl]acetamide	169392-96-5	C₆₅H₈₄FN₅O₂₁	1290.4
——	6-aminohexyl-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-(β-D-galactopyranosyl)-(1->4)-O-[(α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside	167475-62-9	C₃₇H₆₅N₃O₂₃	919.929
——	p-methoxyphenyl O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl) onate]-(2->3)-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glu...	202865-08-5	C₇₂H₇₈Cl₂N₂O₂₇	1474.31
——	methyl (2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5R,6S)-2-[(2R,3S,4R,5R,6R)-5-acetamido-6-(6-azidohexoxy)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-(fluoromethyl)-3,5-dihydroxyoxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	169392-95-4	C₆₆H₈₈FN₅O₂₂	1322.44
——	3-O-(N-acetyl-α-neuraminosyl)deoxoglycyrrhetol	——	C₄₁H₆₇NO₁₀	733.984
——	methyl 3-O-(N-acetyl-α-neuraminosyl)glycyrrhetinate	——	C₄₂H₆₅NO₁₂	775.978
——	3-O-(N-acetyl-β-neuraminosyl)glycyrrhetol	——	C₄₁H₆₅NO₁₁	747.967
——	3-O-(N-acetyl-α-neuraminosyl)glycyrrhetinic acid	——	C₄₁H₆₃NO₁₂	761.951
——	Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester	202865-04-1	C₅₄H₅₃Cl₂NO₁₆	1042.92

反应信息

作为反应物：

描述：

二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯在甲烷磺酸作用下，以甲醇为溶剂，反应 24.0h，生成 (4S,5R,6R)-5-Amino-4-hydroxy-2-methylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

参考文献：

名称：

N-羟甲基神经氨酸（NeuGc的有效供体）的甲基2-硫代糖苷的简便制备物

摘要：

由N-乙酰神经氨酸（NeuAc）分6步合成N-乙酰神经氨酸（SMe-NeuGc，1）的甲基2-硫代糖苷（SMe-NeuGc，1），它是NeuGc在制备唾液酸糖结合物中的有效供体。1可以用两个乳糖受体糖基化以高产率得到唾液酸寡糖8、9和10。

DOI：

10.1016/0040-4039(96)00383-8
作为产物：

描述：

N-acetylneuraminic acid methyl ester 在三氟甲磺酸三甲基硅酯作用下，以吡啶为溶剂，生成二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯

参考文献：

名称：

Chemical and enzymatic synthesis of high-affinity selectin ligands

摘要：

Analogs of sialyl Lewis(x) have been synthesized chemically using donors of modified sialic acids. The sialic acids were obtained enzymatically by an aldolase reaction. The sLe(x) tetrasaccharides modified at C-2 of the GlcNAc moiety and at C-5 of the sialic acid residue were tested as inhibitors for E- and P-selectins. Up to 12-fold higher inhibitory potency was found for the lyse-derivative of sLeX compared to the parent compound. (C) 1997 Elsevier Science Ltd.

DOI：

10.1016/s0960-894x(97)00051-6

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文献信息

Use of dichlorophthaloyl (DCPhth) group as an amino protecting group in oligosaccharide synthesis

作者：Matthias Lergenmüller、Yukishige Ito、Tomoya Ogawa

DOI：10.1016/s0040-4020(97)10377-5

日期：1998.2

As an alternative to phthaloyl (Phth) group, 4,5-dichlorophthaloyl (DCPhth) group was investigated as an amino protecting group to prove it to be useful for the synthesis of β-glycosides of 2-acetamido-2-deoxy glucose (GlcNAc). DCPhth was introduced onto the C-2 nitrogen of glucosamine to give 2, which was further transformed into mono- and di- and trisaccharide derivatives which constitute basic structural

作为邻苯二甲酰基（Phth）基团的替代品，研究了4,5-二氯邻苯二甲酰基（DCPhth）基团作为氨基保护基，证明其可用于合成2-乙酰氨基-2-脱氧葡萄糖（GlcNAc）的β-糖苷。）。将DCPhth引入到葡萄糖胺的C-2氮上，得到2进一步转化成构成天冬酰胺连接的糖蛋白寡糖的基本结构单元的单糖，二糖和三糖衍生物。DCPhth基团在保护基操作（例如脱乙酰基，苄基化，苄基化）和路易斯酸，银盐和碘鎓离子促进的糖基化的标准条件下证明具有足够的稳定性。通过在乙醇溶剂中使用乙二胺，在对Phth进行脱保护所需的实质上较温和的条件下，顺利地除去DCPhth基团。
A Fragment-Based In Situ Combinatorial Approach To Identify High-Affinity Ligands for Unknown Binding Sites

作者：Sachin V. Shelke、Brian Cutting、Xiaohua Jiang、Hendrik Koliwer-Brandl、Daniel S. Strasser、Oliver Schwardt、Soerge Kelm、Beat Ernst

DOI：10.1002/anie.200907254

日期：——

the lead: The title method for the identification of ligands is particularly useful for binding sites where little or no structural information is available. In a fragment‐based approach, a suitable pair of first‐ and second‐site ligands is identified by NMR experiments. By applying a receptor‐mediated in situ combinatorial approach, the two ligands are then linked to generate a new high‐affinity lead

潜在客户：鉴定配体的标题方法特别适用于很少或没有结构信息的结合位点。在基于片段的方法中，通过NMR实验确定了合适的一对第一位和第二位配体。通过应用受体介导的原位组合方法，然后将两个配体连接起来以生成新的高亲和力铅结构（参见图片）。
Synthesis of Simple Sea Cucumber Ganglioside Analogs

作者：Ryuichi Higuchi、Takeshi Mori、Tetsuji Sugata、Koji Yamada、Tomofumi Miyamoto

DOI：10.1002/(sici)1099-0690(199911)1999:11<3175::aid-ejoc3175>3.0.co;2-o

日期：1999.11

Two simple sea cucumber ganglioside analogs 8(NeuAcα 26 Glcβ 1 docosanol) and 9 (NeuAcβ 26 Glcβ 11 docosanol), containing a long-chain alcohol as a mimic of ceramide, have been synthesized. Coupling of the methyl 2-thioglycoside derivative of N-acetylneuraminic acid 5 with docosyl glucoside derivative 3 afforded the protected ganglioside analogs 6and 7, which were deprotected to give the corresponding

合成了两个简单的海参神经节苷脂类似物8（NeuAcα26Glcβ1二十二烷醇）和9（NeuAcβ26Glcβ11二十二烷醇），它们含有长链醇作为神经酰胺的模拟物。N-乙酰神经氨酸5的甲基2-硫代糖苷衍生物与二十二烷基葡糖苷衍生物3的偶联提供了被保护的神经节苷脂类似物6和7，其被脱保护以分别得到相应的神经节苷脂类似物8和9。这些端基异构体8和9的13 C-NMR数据证明对确定神经节苷脂中唾液酸残基的异头构型很有用。
Synthesis and anti-influenza virus evaluation of triterpene-sialic acid conjugates

作者：Mitsuru Tsuji、Nongluk Sriwilaijaroen、Hideo Inoue、Kazuhiko Miki、Kaoru Kinoshita、Kiyotaka Koyama、Kimio Furuhata、Yasuo Suzuki、Kunio Takahashi

DOI：10.1016/j.bmc.2017.09.038

日期：2018.1

new non-natural glycosides with sialic acid conjugates and their biological activities. We report the synthesis of eleven non-natural occurring glycosides, which are triterpene (glycyrrhetinic acid and its derivatives)-sialic acid conjugates, and their inhibitory activities against influenza virus sialidases and influenza virus multiplication in MDCK host cells. Deoxoglycyrrhetol-sialic acid conjugates

我们对具有唾液酸缀合物的新型非天然糖苷及其生物学活性感兴趣。我们报告了十一种非天然糖苷的合成，它们是三萜（甘草次酸及其衍生物）-唾液酸缀合物，以及它们对流感病毒唾液酸酶和MDCK宿主细胞中流感病毒繁殖的抑制活性。Deoxoglycyrrhetol-唾液酸结合物（6d和6e）和齐墩果酸-唾液酸结合物（7d和7e）显示出对三种亚型流感病毒唾液酸酶的强抑制活性。这四种化合物（6d，6e，7d和7e）对流感病毒的增殖表现出明显的抑制作用，但对MDCK宿主细胞的存活没有抑制作用。
Chemo-Enzymatic Synthesis of Antagonists of the Myelin-associated Glycoprotein (MAG)

作者：Gan-Pan Gao、Oliver Schwardt、Tamara Visekruna、Said Rabbani、Beat Ernst

DOI：10.2533/000942904777678019

日期：——

Ganglioside GQ1b ? is the most potent antagonist of the Myelin-associated glycoprotein (MAG) identified so far. For the efficient synthesis of the partial structure of GQ1b ? and derivatives thereof, a chemo-enzymatic strategy using the ?(2?3)-sialyltransferase ratST3Gal III (EC 2.4.99.6) was applied. Besides the natural substrates Gal? (1?3)GlcNAc (19) and Gal? (1?4)GlcNAc (20), the disaccharides Gal? (1?3)GalNTCA?-OSE (9), Gal? (1?3)GalNAc?-OSE (11), and Gal? (1?3)Gal?-OSE (14) were also tolerated by the enzyme and were transformed to the target structures in preparative scale.

GQ1b神经节苷脂是迄今为止发现的髓鞘相关糖蛋白（MAG）中最强效的拮抗剂。为了高效合成GQ1b的部分结构及其衍生物，采用了一种化学-酶联合策略，利用了（2-3）-唾液酸转移酶ratST3Gal III（EC 2.4.99.6）。除了天然底物Gal（1-3）GlcNAc和Gal（1-4）GlcNAc之外，二糖Gal（1-3）GalNTCA- OSE、Gal（1-3）GalNAc- OSE和Gal（1-3）Gal- OSE也被酶耐受，并在制备规模下转化为目标结构。