methyl 6-deoxy-β-lactoside | 86520-75-4

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 6-deoxy-β-lactoside

英文别名

Methyl 6-deoxy-4-O-I(2)-D-galactopyranosyl-I(2)-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2-methyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

CAS

86520-75-4

化学式

C₁₃H₂₄O₁₀

mdl

——

分子量

340.328

InChiKey

YTKBKMQYJFNIML-ABBMIVAOSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

588.2±50.0 °C(Predicted)
密度：

1.53±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-3.72
重原子数：

23.0
可旋转键数：

4.0
环数：

2.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

158.3
氢给体数：

6.0
氢受体数：

10.0

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
——	methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside	147664-43-5	C₂₅H₃₆O₁₇	608.551
——	methyl 2,3-di-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside	147664-47-9	C₂₅H₃₆O₁₆	592.551
——	1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose	——	C₂₈H₃₈O₁₉	678.598
beta-D-半乳糖五乙酸酯	β-D-galactose peracetate	4163-60-4	C₁₆H₂₂O₁₁	390.344
甲基 4-O-[4,6-O-(苯基亚甲基)-beta-D-半乳糖基]-beta-D-吡喃葡萄糖苷	methyl 4',6'-O-benzylidene-β-lactoside	56865-31-7	C₂₀H₂₈O₁₁	444.436
——	methyl 2,3-di-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-β-galactopyranosyl)-β-D-glucopyranoside	42015-30-5	C₂₅H₃₅IO₁₆	718.448
——	methyl 2,3-di-O-benzyl-6-deoxy-β-D-glucopyranoside	176380-03-3	C₂₁H₂₆O₅	358.434
——	Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester	176380-06-6	C₃₅H₄₄O₁₄	688.726
——	methyl 4',6'-O-benzylidene-6-deoxy-6-iodo-β-lactoside	144368-52-5	C₂₀H₂₇IO₁₀	554.333
——	Hepta-O-acetyl-α-D-lactosyl fluoride	14227-57-7	C₂₆H₃₅FO₁₇	638.552

反应信息

作为产物：

描述：

methyl 2,3-di-O-benzyl-6-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 甲醇、三氟甲磺酸三甲基硅酯、 4 A molecular sieve 、氢气、 sodium methylate 作用下，以乙醇、二氯甲烷、溶剂黄146 为溶剂，生成 methyl 6-deoxy-β-lactoside

参考文献：

名称：

与h型2血型决定簇有关的“支链” 2-连接三糖的合成和结构研究

摘要：

一系列岩藻糖基化的三糖l-Fuc-（12）-ß-d-Gal-（14）-ß-X-OMe（1-6，X = d-GlcNAc，d-Qui（6-deoxy-Glc），已经合成了与H 2型血型决定因素有关的d-Xyl），它们分别是α-和ß-L-Fuc异构体以及二糖类起始化合物（7-11）。三糖及其母体二糖的构象性质已通过NMR光谱法（质子和碳化学位移以及质子NOE）结合蒙特卡罗方法和HSEA力场的计算机建模（使用GEGOP程序）进行了研究在α-连接的岩藻糖系列上。

DOI：

10.1560/lxum-gkyp-r6rf-08tf

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文献信息

Studies of the molecular recognition of synthetic methyl β-lactoside analogues by Ricinus communis agglutinin

作者：Alfonso Rivera-Sagredo、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Dolores Solís、Teresa Díaz-Mauriño

DOI：10.1016/0008-6215(92)80055-6

日期：1992.8

The 2-, 3-, 6-, 2'-, 3'-, 4'-, and 6'-deoxy derivatives and the 3-O-methyl derivative of methyl beta-lactoside have been synthesised and their binding to the galactose-specific agglutinin from Ricinus communis (RCA-120) has been investigated. The results indicate that HO-3,4,6 of the beta-D-galactopyranose moiety are the key polar groups. The main difference from the closely related ricin lectin RCA-60

已经合成了甲基β-乳糖苷的2-，3-，6-，2'-，3'-，4'-和6'-脱氧衍生物和3-O-甲基衍生物，并且它们与半乳糖结合研究了来自蓖麻的特异性凝集素（RCA-120）。结果表明，β-D-吡喃半乳糖部分的HO-3、4、6是关键的极性基团。与紧密相关的蓖麻毒素凝集素RCA-60的主要区别在于D-吡喃葡萄糖部分的HO-6，这似乎有助于碳水化合物与RCA-60的结合而不与RCA-120的结合。
The Function of the 5-Hydroxymethyl Group of Lactose in Enzymatic Hydrolysis with beta-Galactosidase from E. coli.

作者：Kim Adelhorst、Klaus Bock、S. T. Thiilborg、H. M. Nielsen、Fatima M. Piedade、M. M. Kady、S. Brøgger Christensen

DOI：10.3891/acta.chem.scand.46-1114

日期：——

A series of 6-substituted methyl lactoside derivatives together with methyl allolactoside and (6S)-methyl [6-H-2]lactoside have been synthesized and characterized by NMR spectroscopy. All compounds were tested as substrates for the enzyme beta-galactosidase from E. coli using progress curve kinetic methology both in single-substrate and competition experiments. The results show that the hydrolysis of methyl lactoside to a large extent takes place through an intramolecular trans-glycosidation reaction via allolactoside. Furthermore, methyl 6-amino-6-deoxy-D-glucopyranoside proved to be an inhibitor for the enzymatic hydrolysis.