methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 76251-67-7

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

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

英文别名

methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl)-α-D-mannopyranoside；methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]Man(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Man1Me；(2S,3S,4R,5R,6R)-2-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside化学式

CAS

76251-67-7

化学式

C₅₅H₆₀O₁₁

mdl

——

分子量

897.075

InChiKey

BBWPMUKQLZXTPI-WDVUHQPGSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

926.4±65.0 °C(Predicted)
密度：

1.25±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

7.4
重原子数：

66
可旋转键数：

23
环数：

8.0
sp3杂化的碳原子比例：

0.35
拓扑面积：

113
氢给体数：

1
氢受体数：

11

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
((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇	methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside	34212-64-1	C₂₈H₃₂O₆	464.558
——	3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose	68681-00-5	C₃₀H₃₄O₇	506.596
3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯)	3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose	16697-49-7	C₃₀H₃₄O₇	506.596
——	1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose	71696-32-7	C₂₇H₂₈O₅	432.516
甲基 2,3,4-三-O-苄基-6-O-三苯基甲基-ALPHA-D-吡喃甘露糖苷	(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran	——	C₄₇H₄₆O₆	706.879
——	2-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-mannopyranosyl trichloroacetimidate	187226-47-7	C₃₁H₃₂Cl₃NO₇	636.957
——	methyl 6-O-trityl-α-D-mannopyranoside	20231-36-1	C₂₆H₂₈O₆	436.505
甲基-D-丙噻	(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol	617-04-9	C₇H₁₄O₆	194.185
甲基6-O-[(叔丁基)二苯基硅烷基]-2,3,4-三-O-(苯基甲基)-ALPHA-D-吡喃甘露糖苷	tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane	186540-03-4	C₄₄H₅₀O₆Si	702.963

反应信息

作为反应物：

描述：

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在吡啶、三氟甲磺酸三甲基硅酯作用下，以二氯甲烷为溶剂，反应 3.5h，生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside

参考文献：

名称：

Synthesis of Laminin Hexasaccharide Analogue

摘要：

The synthesis of laminin hexasaccharide analogue di-O-[Gal-beta-(1-->4)-Glc-beta]-(1-->2)-(1-->6)-man-alpha-(1-->6)-man-alpha-Me derivative (1) was achieved with 1,2-anhydro-mannopyranose benzyl ether (3) as the key intermediate. Coupling of 3 with methyl 2,3,4-tri-O-benzyl-alpha-D-mannopyranoside (4) promoted by ZnCl2 gave methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (2a). Selective 6-O-debenzylation of 2b with ZnCl2-Ac2O-HOAc followed by coupling with acetobromolactopyranose afforded 1.

DOI：

10.1080/07328309808007463
作为产物：

描述：

2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖在吡啶、三氟甲磺酸三甲基硅酯、 4 A molecular sieve 、氨、 sodium 、 sodium hydride 、溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯作用下，以甲醇、二氯甲烷、水、 N,N-二甲基甲酰胺为溶剂，反应 94.83h，生成 methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

参考文献：

名称：

Synthesis of a tetrasaccharide fragment of cobra venom factor oligosaccharide

摘要：

Synthesis of a tetrasaccharide fragment, alpha-L-Fuc-(1-->3)-beta-D-GlcNAc-(1-->2)-alpha-D-Man-(1-->6)-alpha-D-Man-OMe of the cobra venom factor (CVF) oligosaccharide is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

DOI：

10.1016/s0008-6215(99)00107-x

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文献信息

Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry

作者：S. Daikoku、R. Pendrill、Y. Kanie、Y. Ito、G. Widmalm、O. Kanie

DOI：10.1039/c7ob02723k

日期：——

mass spectrometry (ERMS), and 1H nuclear magnetic resonance spectroscopy. The CID experiments of sodiated species of disaccharides and ERMS experiments revealed that the order of stability of mannosyl linkages was as follows: 6-linked > 4-linked ≧ 2-linked > 3-linked mannosyl residues. Analysis of linear trisaccharides revealed that the order observed in disaccharides could be applied to higher glycans

使用碰撞诱导解离（CID），能量分辨质谱（ERMS）和1制备了一系列与由α-甘露糖苷组成的与天然存在的和生物学上相关的聚糖相关的化合物H核磁共振波谱学。二糖的糖化物种类的CID实验和ERMS实验显示，甘露糖基键的稳定性的顺序如下：6-连接的> 4-连接的≥2-连接的> 3-连接的甘露糖基残基。线性三糖的分析表明，在二糖中观察到的顺序可以应用于更高的聚糖。支链的三糖显示出明显的解离模式，具有两个构成的二糖离子。使用二糖光谱可以估算该离子混合物的含量。支链三糖中3-位和6-位甘露糖键的水解显示3-键的断裂速度是6-键的两倍。观察到溶液相水解和气相解离具有相似的能量。
Mannose-Binding Geometry of Pradimicin A

作者：Yu Nakagawa、Takashi Doi、Takara Taketani、K. Takegoshi、Yasuhiro Igarashi、Yukishige Ito

DOI：10.1002/chem.201301368

日期：2013.8.5

solid‐state NMR spectroscopy revealed that the C2–C4 region of Man is in close contact with the primary binding site of PRM‐A, while the C1 and C6 positions of Man are relatively distant. The binding geometry was further validated by co‐precipitation experiments using deoxy‐Man derivatives, leading to the proposal that PRM‐A binds not only to terminal Man residues at the non‐reducing end of glycans, but

Pradimicins（PRMs）和benanomicins是唯一具有类凝集素特性的非肽类天然产物家族，也就是说，它们在存在Ca 2+的情况下识别D-甘露吡喃糖苷（Man）。离子。结合其独特的Man结合能力，它们通过与病原体的Man聚糖结合而具有抗真菌和抗HIV的活性。尽管PRM作为凝集素模拟物和治疗先导具有巨大潜力，但它们对Man识别的分子基础尚未建立。它们的聚集体形成倾向阻碍了溶液中的常规相互作用分析，并且由于PRM中存在两个Man结合位点，加剧了分析难度。在这项工作中，我们通过最近开发的分析策略，使用由PRM‐A和Man的1：1配合物组成的固体聚集体，研究了PRMs的原始成员PRM‐A的主要Man结合的几何形状。通过固态NMR光谱对分子间距离的评估表明，Man的C2-C4区与PRM-A的主要结合位点紧密接触，而Man的C1和C6位置相对较远。通过使用脱氧曼衍生物的共沉淀实验进一步验证
Catalytic Cleavage of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group under Neat Conditions

作者：Serena Traboni、Fabiana Esposito、Marcello Ziaco、Noemi De Cesare、Emiliano Bedini、Alfonso Iadonisi

DOI：10.1021/acs.orglett.4c00918

日期：2024.4.19

This work reports the first solvent-free catalytic approach for the cleavage of the fluorenylmethoxycarbonyl (Fmoc) protecting group from amine and alcohol functionalities. Various saccharide, peptide, and glyco-amino acid substrates were efficiently deprotected by simple treatment with 20 mol % neat 4-dimethylaminopyridine (DMAP) (one of the effective base catalysts found), without any solvent or

这项工作报告了第一个无溶剂催化方法，用于从胺和醇官能团中裂解芴基甲氧基羰基 (Fmoc) 保护基团。通过用 20 mol% 纯 4-二甲基氨基吡啶 (DMAP)（已发现的有效碱催化剂之一）进行简单处理，即可有效脱除各种糖、肽和糖基氨基酸底物，无需任何溶剂或化学计量添加剂。最终通过一锅法、碱催化、无溶剂多步序列将 Fmoc 裂解与酯化、酰胺化和/或糖基化步骤相结合，组装出小型模型结构。
Synthesis of galactosyl and lactosyl derivatives as potential anti-metastasis compounds

作者：Hui Li、Qing Li、Meng-Shen Cai、Zhong-Jun Li

DOI：10.1016/s0008-6215(00)00137-3

日期：2000.10

Based on the known anti-metastasis activities of lactosides and galactosides, a galactosyl and a lactosyl trimannoside were prepared via the conventional Koenigs-Knorr and trichloroacetimidate methods, respectively. Through typical deblocking procedures, a tetrasaccharide alpha-D-Galp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) and a pentasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.
Synthesis of .beta.-D-mannopyranosides and .beta.-L-rhamnopyranosides by glycosidation at C-1

作者：Vinai K. Srivastava、Conrad Schuerch

DOI：10.1021/jo00319a016

日期：1981.3