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3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol | 28069-18-3

分子结构分类

有机化合物 - 脂质和类脂质分子 - 甘油脂

中文名称

——

中文别名

——

英文名称

3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol

英文别名

1-(1’-β-D-[2’,3’,4’,6’-tetracetyl]galactosyl)glycerol；β-D-galactosylglycerol；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,3-dihydroxypropoxy)oxan-2-yl]methyl acetate

3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol化学式

CAS

28069-18-3

化学式

C₁₇H₂₆O₁₂

mdl

——

分子量

422.386

InChiKey

QQMKBKAGKNLWMX-HUVXYLLVSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

533.7±50.0 °C(Predicted)
密度：

1.35±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.7
重原子数：

29
可旋转键数：

13
环数：

1.0
sp3杂化的碳原子比例：

0.76
拓扑面积：

164
氢给体数：

2
氢受体数：

12

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
——	1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose	28152-35-4	C₂₀H₃₀O₁₂	462.451
2,3,4,6-O-四乙酰基-D-半乳糖	2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose	47339-09-3	C₁₄H₂₀O₁₀	348.307
——	allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside	54400-76-9	C₁₇H₂₄O₁₀	388.372
1,2,3,4,6-D-葡萄糖五乙酸酯	D-galactose pentaacetate	25878-60-8	C₁₆H₂₂O₁₁	390.344
beta-D-半乳糖五乙酸酯	β-D-galactose peracetate	4163-60-4	C₁₆H₂₂O₁₁	390.344
2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯	2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate	86520-63-0	C₁₆H₂₀Cl₃NO₁₀	492.695
D-吡喃葡萄糖	D-Galactose	10257-28-0	C₆H₁₂O₆	180.158

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(2R)-1-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol	42869-31-8	C₁₇H₂₆O₁₂	422.386
——	(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)acetic acid	206053-56-7	C₁₆H₂₂O₁₁	390.344
——	Docosanoic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester	651306-10-4	C₃₉H₆₈O₁₃	744.961
——	(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-hydroxy-3-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1357286-91-9	C₃₅H₆₀O₁₃	688.854
——	1,2-O-dilauroyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol	651306-24-0	C₄₁H₇₀O₁₄	786.998
——	1,2-di-O-palmitoyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-rac-glycerol	28069-22-9	C₄₉H₈₆O₁₄	899.213
——	(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2,3-bis(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1357286-90-8	C₅₃H₉₄O₁₄	955.321
——	(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-hydroxy-3-(((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl)oxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1613026-83-7	C₃₇H₅₆O₁₃	708.844
——	(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid 2-hydroxy-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester	651306-11-5	C₃₅H₅₄O₁₃	682.806
——	1,2-O-dilinoleoyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol	652149-88-7	C₅₃H₈₆O₁₄	947.257
——	(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-3-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1357286-92-0	C₅₃H₈₈O₁₄	949.273
——	1-O-linolenoyl-2-O-linoleoyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol	651306-26-2	C₅₃H₈₄O₁₄	945.242
——	(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(3-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-2-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate	1357286-87-3	C₅₃H₈₈O₁₄	949.273
——	[2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate	1357286-86-2	C₅₃H₈₂O₁₄	943.226
——	O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone	206053-58-9	C₁₇H₂₅N₃O₁₀S	463.466
——	1,2-O-dilauroyl-3-O-β-D-galactopyranosyl-rac-glycerol	——	C₃₃H₆₂O₁₀	618.849
单半乳糖甘油二酯	1,2-O-distearoyl-3-O-(β-D-galactopyranosyl)glycerol	41670-62-6	C₄₅H₈₆O₁₀	787.172
——	(2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside	1402142-31-7	C₂₀H₂₆O₁₂	458.419
——	(2,3-dihydro-4-oxo-4H-pyran-2-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside	1402142-30-6	C₂₀H₂₆O₁₂	458.419
——	1-O-linolenoyl-2-O-stearoyl-3-O-β-D-galactopyranosylglycerol	——	C₄₅H₈₀O₁₀	781.124
——	[2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate	1357286-94-2	C₄₅H₈₀O₁₀	781.124
——	(2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-β-D-galactopyranosyl glycerol	——	C₄₅H₇₄O₁₀	775.077
——	1-0-stearic acid-3-0-β-D-galactopyranoside glyceride	35949-83-8	C₂₇H₅₂O₉	520.704
——	((2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol)	420840-09-1	C₂₇H₄₆O₉	514.657
——	4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose	1402142-38-4	C₃₄H₄₄O₂₂	804.71
——	4,6-di-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-L-threo-hex-1-en-3-ulose	1402142-34-0	C₃₄H₄₄O₂₂	804.71
——	O-(β-D-galactopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone	——	C₉H₁₇N₃O₆S	295.316

反应信息

作为反应物：

描述：

3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol 在 4-二甲氨基吡啶、 N,N'-二环己基碳二亚胺作用下，以二氯甲烷为溶剂，生成 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-3-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

参考文献：

名称：

An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids

摘要：

Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.tetlet.2011.12.030
作为产物：

描述：

D-吡喃葡萄糖在四氧化锇、三氟化硼乙醚、 sodium acetate 、 N-甲基吗啉氧化物作用下，以四氢呋喃、二氯甲烷、水、叔丁醇为溶剂，反应 26.25h，生成 3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol

参考文献：

名称：

两个单糖单元的异狄尔斯-阿尔德焊接合成三糖

摘要：

提出了一种基于连接糖单元从头合成的二糖和三糖合成新策略。在该策略中，已经结合糖苷键的功能化单糖构建块使用金属催化的异狄尔斯-阿尔德 (HDA) 反应焊接在一起，以在它们之间生成新的单糖单元。HDA 反应的最高产率和选择性是通过使用手性席夫碱铬配合物获得的。二糖产物可通过Danishefsky's 二烯与乙酰基和苄基保护的半乳糖苷醛反应获得。为了合成三糖产品，使用铬催化剂将乙酰保护的葡萄糖或半乳糖衍生的二烯与单糖衍生的醛融合以进行 HDA 反应。以中等至良好的收率获得了所需的三糖产品，并具有出色的立体选择性。根据核磁共振光谱和模型研究，在该过程中产生的中心吡喃酮糖环具有 L-顺式-烯酮糖构型。

DOI：

10.1002/ejoc.201200277

点击查看最新优质反应信息

文献信息

Synthesis and polymorphism of deuterium labeled unsaturated monogalactosyl diglyceride as studied by 2H NMR

作者：Vladimir Chupin、Svetlana Smirnova、Ben de Kruijff

DOI：10.1002/recl.19941130412

日期：——

The synthesis and polymorphism of deuterium-labeled 1,2-di-O-[11-2H2)-oleoyl]-3-O-β-D-galactopyranosyl)-rac-glycerol is described. 2H-NMR studies show that this lipid in its hydrated state adopts a lamellar phase below - 5°C and an inverted hexagonal phase above - 5°C.

的氘标记的1,2-二-合成和多态性ö - [11- 2 ħ 2） -油酰基] -3- ö -β-d吡喃半乳糖基） -外消旋-甘油进行说明。2 H-NMR研究表明，处于水合状态的该脂质在低于-5℃的温度下为层状相，在高于-5℃的温度下为倒六角相。
GLYCEROL CARBONATE GLYCOSIDE

申请人：KAO CORPORATION

公开号：EP1674476B1

公开（公告）日：2012-06-20
Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides

作者：Wicharn Janwitayanuchit、Khanit Suwanborirux、Chamnan Patarapanich、Sunibhond Pummangura、Vimolmas Lipipun、Tirayut Vilaivan

DOI：10.1016/j.phytochem.2003.09.008

日期：2003.12

Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
Design and synthesis of fluorescent galactolipid probes

作者：Emiliano Manzo、Giuliana D’Ippolito、Dario Pagano、Francesco Tinto、Angelo Fontana

DOI：10.1016/j.tetlet.2014.04.059

日期：2014.6
Evstigneeva, R. P.; Lyubeshkin, A. V.; Anikin, M. V., Doklady Chemistry, 1993, vol. 330, # 1-3, p. 119 - 123

作者：Evstigneeva, R. P.、Lyubeshkin, A. V.、Anikin, M. V.、Sebyakin, Yu. L.、Barkhudaryan, M. S.、et al.

DOI：——

日期：——