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propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 83476-52-2

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

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

英文别名

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose；2-propynyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；prop-2-ynyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；Propargyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside化学式

CAS

83476-52-2

化学式

C₁₇H₂₂O₁₀

mdl

——

分子量

386.356

InChiKey

HKGFUJKLPCRVFW-NRKLIOEPSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

100 °C
沸点：

449.4±45.0 °C(Predicted)
密度：

1.27±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.7
重原子数：

27
可旋转键数：

11
环数：

1.0
sp3杂化的碳原子比例：

0.65
拓扑面积：

124
氢给体数：

0
氢受体数：

10

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
2,3,4,6-O-四乙酰基-D-吡喃甘露糖	2,3,4,6-tetra-O-acetyl-D-mannopyranose	140147-37-1	C₁₄H₂₀O₁₀	348.307
Α-D-五乙酸甘露糖酯	D-Mannose pentaacetate	25941-03-1	C₁₆H₂₂O₁₁	390.344
1,2,3,4,6-O-五乙酰基-Alpha-甘露糖	per-O-acetyl-α-D-mannopyranose	4163-65-9	C₁₆H₂₂O₁₁	390.344
炔丙基α-D-吡喃甘露糖苷	propargyl α-D-mannopyranoside	854262-01-4	C₉H₁₄O₆	218.207
——	propargyl D-mannopyranoside	——	C₉H₁₄O₆	218.207
2,3,4,6-四-O-乙酰基-α-D-吡喃甘露糖三氯乙酰亚胺酯	2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate	121238-27-5	C₁₆H₂₀Cl₃NO₁₀	492.695
D-甘露糖	alpha-D-mannopyranoside	7296-15-3	C₆H₁₂O₆	180.158
甘露糖	D-Mannose	530-26-7	C₆H₁₂O₆	180.158

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	propargyl 3,4,6-tri-O-acetyl-α-D-mannopyranoside	1159265-86-7	C₁₅H₂₀O₉	344.318
——	6-methoxyhexa-2,4-diynyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	1269016-65-0	C₂₁H₂₆O₁₁	454.431
——	2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	617691-71-1	C₁₆H₂₄O₁₁	392.36
——	3-hydroxypropyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	494844-22-3	C₁₇H₂₆O₁₁	406.387
——	1-propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	722544-09-4	C₁₇H₂₆O₁₀	390.387
——	2-(allyloxy)ethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	1402076-80-5	C₁₉H₂₈O₁₁	432.425
烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷	allyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	119111-31-8	C₁₇H₂₄O₁₀	388.372
——	(3-(((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)prop-1-en-1-yl)boronic acid	1426912-51-7	C₁₇H₂₅BO₁₂	432.189
——	[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[3-[4-[3-[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]prop-2-ynoxy]oxan-2-yl]methyl acetate	287967-83-3	C₄₀H₄₆O₂₀	846.793
——	3-(benzyloxy)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	948297-90-3	C₂₄H₃₂O₁₁	496.511
——	1,3-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene	1318797-52-2	C₄₀H₄₆O₂₀	846.793
——	2-propynyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside	854261-90-8	C₁₅H₂₂O₆	298.336
——	1,2-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene	1318797-51-1	C₄₀H₄₆O₂₀	846.793
炔丙基α-D-吡喃甘露糖苷	propargyl α-D-mannopyranoside	854262-01-4	C₉H₁₄O₆	218.207
——	(2S,3S,4S,5R,6R)-2-((3-(1,3,6,2-dioxazaborocan-2-yl)allyl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1426912-49-3	C₂₁H₃₂BNO₁₂	501.296
——	propargyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside	1253191-75-1	C₃₀H₂₆O₉	530.531
——	(2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1426912-47-1	C₂₃H₃₅BO₁₂	514.335
烯丙基alpha-D-吡喃甘露糖苷	allyl α-D-mannopyranoside	41308-76-3	C₉H₁₆O₆	220.222
——	2-oxopropyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside	403738-05-6	C₃₇H₄₀O₇	596.72
——	Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester	83476-63-5	C₅₁H₆₆O₃₀	1159.07
——	(3-(((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)prop-1-en-1-yl)boronic acid	1426912-53-9	C₉H₁₇BO₈	264.04
——	1,3-bis[3-(α-D-mannopyranosyloxy)prop-1-ynyl]benzene	871311-21-6	C₂₄H₃₀O₁₂	510.495
——	2-propynyl 2,3,4-tri-O-acetyl-6-O-tosyl-α-D-mannopyranoside	1141387-58-7	C₂₂H₂₆O₁₁S	498.508
——	1,2-bis[3-(α-D-mannopyranosyloxy)prop-1-ynyl]benzene	871311-20-5	C₂₄H₃₀O₁₂	510.495
——	Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[3-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-phenoxy}-tetrahydro-pyran-3-yl ester	287967-77-5	C₃₇H₄₄O₂₀	808.744
——	4-phenyl-1,7-bis-O-[2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl]hep-2,5-diyn-1,4,7-triol	854261-91-9	C₃₇H₄₈O₁₃	700.78
——	1-(2-hydroxyethyl)-4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxymethyl)-1H-1,2,3-triazole	1167422-09-4	C₁₉H₂₇N₃O₁₁	473.437
——	1,7-bis-O-[2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl]-4-(p-4-tert-butylphenyloxymethyl)-hep-2,5-diyn-1,4,7-triol	854261-93-1	C₄₂H₅₈O₁₄	786.914
——	1,4-bis-[1,7-di-O-(2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl)hep-2,5-diyn-1,4,7-triol-4-yl]benzene	854261-95-3	C₆₈H₉₀O₂₆	1323.45
——	1,2-bis{[(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyloxyl)methyl]-1H-1,2,3-triazolethoxy}ethane	1403350-79-7	C₄₀H₅₆N₆O₂₂	972.912
——	3,5-bis(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxymethyl)isoxazole	867288-15-1	C₃₃H₄₃NO₂₁	789.699
——	3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-oxymethyl)-5-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-oxymethyl) isoxazole	867288-13-9	C₃₃H₄₃NO₂₁	789.699
——	2-O-phthalimidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	1385773-88-5	C₂₄H₂₇NO₁₃	537.477
——	3-(phthalimidoxy)propyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	948297-77-6	C₂₅H₂₉NO₁₃	551.504
——	1,15-dichloro-8,8-bis[7-{4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxymethyl)-1H-1,2,3-triazol-1-yl}-2,5-dioxahept-1-yl]-3,6,10,13-tetraoxapentadecane	1167422-28-7	C₅₅H₈₄Cl₂N₆O₂₈	1348.2
——	1,3-bis-[1,7-di-O-(2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl)hep-2,5-diyn-1,4,7-triol-4-yl]benzene	854261-97-5	C₆₈H₉₀O₂₆	1323.45
——	[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[(1-benzyltriazol-4-yl)methoxy]oxan-2-yl]methyl acetate	1379046-85-1	C₂₄H₂₉N₃O₁₀	519.508
——	1,4-bis{4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxymethyl)-1H-1,2,3-triazol-1-ylmethyl}benzene	1167992-39-3	C₄₂H₅₂N₆O₂₀	960.903
——	[1-(pyridin-4-yl)-1,2,3-triazol-4-yl]methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside	1345018-89-4	C₂₂H₂₆N₄O₁₀	506.469
——	3-hydroxypropyl 2,3,4,6-tetrakis-O-[tert-butyl(dimethyl)silyl]-α-D-mannopyranoside	948297-88-9	C₃₃H₇₄O₇Si₄	695.288

反应信息

作为反应物：

描述：

propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下，以甲醇为溶剂，反应 12.0h，以100%的产率得到炔丙基α-D-吡喃甘露糖苷

参考文献：

名称：

两亲性 Janus Glycodendrimers 的模块化合成及其自组装成 Glycodendrimersomes 和其他对生物医学相关凝集素具有生物活性的复杂结构

摘要：

报告了 7 个文库的模块化合成，该文库包含 51 个自组装两亲两性树枝状聚合物，其亲水部分含有单糖 D-甘露糖和 D-半乳糖以及双糖 D-乳糖。这些史无前例的含糖树枝状聚合物被命名为两亲性 Janus 树枝状聚合物。它们通过简单地将 THF 或乙醇溶液注入水或缓冲液中并通过水合进行自组装，通过动态光散射、共聚焦显微镜、低温透射电子显微镜、傅里叶变换分析和微量吸管抽吸实验等方法的组合进行分析，以评估机械性能。这些文库揭示了硬和软组件的多样性，包括单层球形、多边形和管状囊泡，称为糖树体，Janus glycodendrimer 和棒状胶束的聚集体称为 glycodendrimer 聚集体和 glycodendrimermicelles，cubosomes 表示 glycodendrimercubosomes 和固体薄片。这些组件在水中和缓冲液中随着时间的推移是稳定的，表现出窄的分子量分布，并显

DOI：

10.1021/ja403323y
作为产物：

描述：

1,2,3,4,6-O-五乙酰基-Alpha-甘露糖在三氟甲磺酸三甲基硅酯、 ammonium acetate 作用下，以二氯甲烷、 N,N-二甲基甲酰胺为溶剂，生成 propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

参考文献：

名称：

Synthesis of novel types of polyester glycodendrimers as potential inhibitors of urinary tract infections

摘要：

这里呈现了具有2、4、8和16个α-甘霍糖残基的高度甘露聚酯树状分子的合成，它们的外围由不同的连接臂连接。

DOI：

10.1039/c4nj00992d

点击查看最新优质反应信息

文献信息

Copper-catalyzed one-pot synthesis of glycosylated iminocoumarins and 3-triazolyl-2-iminocoumarins

作者：Pintu Kumar Mandal

DOI：10.1039/c3ra46844e

日期：——

general strategy was developed for the synthesis of glycosyl iminocoumarins (5a–x) in a one-pot, copper-catalyzed multicomponent reaction involving a domino reaction of sulfonyl azides, sugar alkynes, and salicylaldehydes via ketenimine intermediate formation. Similarly, glycosyl 3-triazolyl-2-iminocoumarin derivatives (6a–o) have also been synthesized in a one-pot, three component condensation via tandem

已开发了在单罐，铜催化的多组分反应中合成糖基亚氨基香豆素（5a–x）的通用策略，该反应涉及通过乙炔亚胺中间体形成的磺酰叠氮化物，糖炔和水杨醛的多米诺反应。同样，糖基3-三唑基-2-亚氨基香豆素衍生物（6a-o）也已通过串联的“ CuAAC-醛醇-环化-脱水”序列以一锅，三组分缩合的方式合成。在这种情况下，2-叠氮基乙腈和糖炔之间的铜催化环加成反应可原位提供三唑衍生物。并活化了相邻的亚甲基，在水杨醛存在下诱导了羟醛-环化-脱水序列。在所有反应中收率都非常好。
Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks

作者：Lisa Tanzi、Marina Simona Robescu、Sara Marzatico、Teresa Recca、Yongmin Zhang、Marco Terreni、Teodora Bavaro

DOI：10.3390/molecules25235764

日期：——

position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently

通过酶水解实现了异头位置不同官能化的乙酰化甘露糖基单糖和二糖的区域选择性脱保护。假丝酵母脂肪酶 (CRL) 和短小芽孢杆菌乙酰木聚糖酯酶 (AXE) 分别固定在辛基琼脂糖和乙醛糖琼脂糖上。生物催化剂的区域选择性受糖结构和异头位置的官能化影响。通常，CRL 能够催化 C6 位乙酰化单糖的区域选择性脱保护。当乙酰化二糖用作底物时，AX 表现出对 C2 或 C6 位置的显着偏好，当 C2 参与糖苷键时。通过在活性和区域选择性方面为每种底物选择最佳酶，
Mannose-based graft polyesters with tunable binding affinity to concanavalin A

作者：Yixuan Xie、Chao Peng、Yunyi Gao、Xiaohong Liu、Tianbo Liu、Abraham Joy

DOI：10.1002/pola.28776

日期：2017.12.1

turbidimetry binding assay showed that graft polyesters with longer mannose graft exhibit higher initial binding rate (ki). Isothermal titration calorimetry measurements of these graft polyesters with Con A showed that polymers exhibit higher binding affinity (ka) with the number of side chain mannose. This study provides understanding of the interaction between Con A and mannose‐based graft polyesters, which

含糖聚合物已被广泛用于理解碳水化合物与凝集素之间的相互作用，这有助于疾病和病原体的诊断和检测以及疫苗的开发。尽管研究的重点是糖聚合物结构及其与凝集素结合的相关性，但接枝型糖聚酯并不常见。本文中，我们报告了“接枝”方法设计和合成基于甘露糖的接枝聚酯，并研究了它们与伴刀豆球蛋白A（Con A）的相互作用。通过1 H NMR光谱法和硫酸-UV方法证实，成功合成了不同长度的甘露糖接枝物。比浊法结合试验的结果表明，甘露糖接枝时间较长的接枝聚酯表现出较高的初始结合率（k i）。这些具有Con A的接枝聚酯的等温滴定量热法测量表明，随着侧链甘露糖数量的增加，聚合物表现出更高的结合亲和力（k a）。这项研究提供了对Con A和基于甘露糖的接枝聚酯之间相互作用的理解，可用于开发糖聚合疗法。©2017 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2017年，55，3908-3917
[EN] MODULAR SYNTHESIS OF AMPHIPHILIC JANUS GLYCODENDRIMERS AND THEIR SELF-ASSEMBLY INTO GLYCODENDRIMERSOMES<br/>[FR] SYNTHÈSE MODULAIRE DE GLYCODENDRIMÈRES AMPHIPHILES DE TYPE JANUS ET LEUR AUTOASSEMBLAGE EN GLYCODENDRIMÈRESOMES

申请人：PERCEC VIRGIL

公开号：WO2014190024A1

公开（公告）日：2014-11-27

The invention concerns compounds of the formula (I) wherein: Y1 and Y2 are independently a monosaccharide or disaccharide; X1 and X2 are independently -(R9-O)m-, -(R10)P-, -O-(R11-O)q-, -R16-O-R17-O- or a covalent bond; Q1 and Q2 are independently a nitrogen-containing heterocycle moiety; Z1 and Z2 are independently -(O-R7)-, -(O-C(=O)-R8)a-, -O-C(=O)-R12-C(=0)-R13-, -O- C(=O)-R14-C(=O)-R15 or a covalent bond; R7-R17 are each independently C1-C6 alkyl; R1-R6 are each independently a linear or branched alkly group; b, c, d, e, f, and g are 0 or 1, provided b + c + d equals at least 2 and e + f + g equals at least 2; and a, m, p, and q are each an integer from 1-6.

该发明涉及式(I)的化合物，其中：Y1和Y2分别是单糖或二糖；X1和X2分别是-(R9-O)m-，-(R10)P-，-O-(R11-O)q-，-R16-O-R17-O-或共价键；Q1和Q2分别是含氮杂环基；Z1和Z2分别是-(O-R7)-，-(O-C(=O)-R8)a-，-O-C(=O)-R12-C(=0)-R13-，-O- C(=O)-R14-C(=O)-R15或共价键；R7-R17各自独立地是C1-C6烷基；R1-R6各自独立地是线性或支链烷基；b、c、d、e、f和g为0或1，但要求b + c + d至少等于2，e + f + g至少等于2；a、m、p和q各自是1-6的整数。
Carbohydrate-naphthalene diimide conjugates as potential antiparasitic drugs: Synthesis, evaluation and structure-activity studies

作者：M. Zuffo、A. Stucchi、J. Campos-Salinas、M. Cabello-Donayre、M. Martínez-García、E. Belmonte-Reche、J.M. Pérez-Victoria、J.L. Mergny、M. Freccero、J.C. Morales、F. Doria

DOI：10.1016/j.ejmech.2018.11.043

日期：2019.2

organisms contain multiple putative G-quadruplex (G4) forming sequences which have recently been proposed to mediate processes relevant for parasite survival. Therefore, G4 could be considered as potential targets for a novel approach towards the development of antiparasitic drugs. Recently, we have demonstrated that G4 ligands such as carbohydrate naphthalene diimide conjugates (carb-NDIs) possess notable

人类非洲锥虫病和利什曼病被忽视的热带病是由锥虫，布鲁氏锥虫和利什曼原虫感染引起的spp，分别。这些生物的基因组包含多个推定的G-四链体（G4）形成序列，最近已提出该序列来介导与寄生虫存活相关的过程。因此，G4可以被视为开发抗寄生虫药物的新方法的潜在目标。最近，我们已经证明G4配体，例如碳水化合物萘二酰亚胺共轭物（carb-NDIs）具有显着的抗寄生虫活性。在此，我们合成碳水化合物编程的一个新的家庭，其特点是显著结构性变化，并评估它们的抗寄生虫活性，特别侧重于布氏锥虫。与相关G4序列的相互作用在体外进行了评估通过独立的生物物理方法（在竞争条件下使用双链DNA，圆二色性和荧光滴定进行FRET熔解测定）。最后，流式细胞术和共聚焦显微镜实验表明，结合物表现出对布鲁氏锥虫寄生虫的极好的吸收，其位于细胞核和运动质体中。有希望的抗寄生虫活性和对哺乳动物控制细胞的选择性及其独特的作用机制，使carb-ND