81381-72-8

Usage

Uses

Used in Organic Synthesis:
(4-Methoxyphenyl)methyl beta-D-glucopyranoside is used as a starting material for the synthesis of other compounds due to its unique structure and properties.
Used in Pharmaceutical Research:
(4-Methoxyphenyl)methyl beta-D-glucopyranoside is used as a building block for the production of various bioactive compounds and natural products, contributing to the development of new drugs and pharmaceuticals.

Upstream product

• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 50-99-7 D-glucose 
• 105-13-5 4-Methoxybenzyl alcohol 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 171412-20-7 (4-methoxybenzyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 63-42-3 D-(+)-lactose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 141263-06-1 4-Methoxybenzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 161068-31-1 paramethoxybenzyl 6-O-terbutyldimethylsilyl β-D-galactopyranoside 
• 186038-69-7 p-methoxybenzyl 2,3,4,6-tetra-O-allyl-β-D-galactopyranoside 
• 7296-64-2 β-D-galactopyranoside 
• 123-11-5 4-methoxy-benzaldehyde 
• 142329-97-3 4-methoxybenzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 169237-18-7 4-methoxybenzyl O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-mannopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 118088-80-5 3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-α-D-arabino-hexopyranose 
• 142329-98-4 4-methoxybenzyl O-<3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl>-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 142329-99-5 4-methoxybenzyl O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 171412-27-4 4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranose 
• 142329-95-1 p-methoxybenzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 142329-96-2 4-methoxybenzyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 1384472-22-3 C₂₅H₃₀O₉ 

Relevant academic research and scientific papers

Synthesis of O-1- O-6 Substituted Positional Isomers of d -Glucose-Thioether Ligands and Their Ruthenium Polypyridyl Conjugates

A library of positional isomers of d-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.

A novel strategy to improve the aromatic alcohols tolerance of enzyme for preparative-scale synthesis of natural glycosides

Aromatic alcohols are liable to result in enzyme inactivation. A novel strategy was established for improving the aromatic alcohol tolerance of β-galactosidase (BMG) from Bacillus megaterium YZ08. The half-life of BMG in 200 mM vanillyl alcohol solution was dramatically increased by 9–123 times with the addition of hydrophilic solvents. In 30% DMSO, the reaction concentration of aromatic alcohol could reach up to 300–400 mM, and 0.85–2.44 g of natural glycosides were successfully obtained in 100 mL-scale. The simple and effective strategy shows potential applications when dealing with the preparative-scale exploitation of enzymatic reactions.

HYDROLASE ENZYME SUBSTRATES AND USES THEREOF

The present invention provides novel methods for determining the presence or amount of a hydrolytic enzyme in a sample, based on novel substrates for the enzymes, and also provides compositions and methods that provide highly sensitive assay methods for such hydrolytic enzymes.

HYDROLASE ENZYME SUBSTRATES AND USES THEREOF

The present invention provides novel methods for determining the presence or amount of a hydrolytic enzyme in a sample, based on novel substrates for the enzymes, and also provides compositions and methods that provide highly sensitive assay methods for s

Using ionic liquid cosolvents to improve enzymatic synthesis of arylalkyl β-d-glucopyranosides

Enzymatic synthesis of various arylalkyl β-d-glucopyranosides catalyzed by prune (Prunus domestica) seed meal via reverse hydrolysis in the mixture of organic solvent, ionic liquid (IL) and phosphate buffer was described. Among four hydrophilic organic solvents tested, ethylene glycol diacetate (EGDA) was found to be the most suitable for enzymatic synthesis of salidroside, a bioactive compound of commercial interest, from d-glucose and tyrosol. The effects of the nature of ionic liquids and their contents on the enzymatic glucosylation were studied. The addition of a suitable amount of ILs including denaturing ones was favorable to shift the reaction equilibrium toward the synthesis, thus improving the yields. Among the examined ILs, the novel IL [BMIm]I proved to be the best. And this IL was applied as the solvent in biocatalysis for the first time. The yields were found to be enhanced between 0.2-fold and 0.5-fold after the addition of 10% (v/v) [BMIm]I. In 10% (v/v) [BMIm]I-containing system, the desired arylalkyl β-d-glucopyranosides were synthesized with 15-28% yields, among which salidroside was obtained with a yield of 22%. .

Synthesis, biological activity of salidroside and its analogues

Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs-Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl) methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4-desmethoxyepisilvestrol

Total synthesis of the anticancer 1,4-dioxane containing natural products silvestrol (1) and episilvestrol (2) is described by an approach basedon the proposed biosynthesis of these novel compounds. The key steps in cluded an oxidative rearrangement of the protected D-glucose derivative 11 to afford the 1,4-dioxane 12, which could be elaborated to the coupling partner 5 and a photochemical [3 + 2] cycloadditon between the 3-hydroxyflavone 27 and methyl cinnamate followed by base-induced α-ketol rearrangement and reduction to give the cyclopentabenzofuran core 33. The core (-)-6 and 1,4-dioxane fragment 5 were united by a highly stereoselective Mitsunobu coupling with the modified azodicarboxylate DMEAD toafford the axial coupled product 36. Deprotection then gave episilvestr ol (2). Silvestrol (1) was synthesized by a coupling between core (-)-6 and the dioxane 44 followed by deprotection. Compound 1 was also synthesized from episilvestrol (2) by a Mitsunobu inversion. In addition, the analogue 4-desmethoxyepisilvestrol (46) was synthesized via the same route. It was found that 46 and episilvestrol 2 displayed an unexpected concentration-dependent chemical shift variation for the nonexchangeable dioxane protons. Synthetic compounds 1, 2, 38, 46, and 54 were tested against cancer cells lines, and it was found that the stereochemistry of the core was critical for activity. Synthetic analogue 4-desmethoxyepisilvestrol (46) was also active against lung and colon cancer cell lines.

Total synthesis of (-)-episilvestrol and (-)-silvestrol

Sugar and spice... The total synthesis of the rare but potent anticancer natural product (-)-episilvestrol and its 5? epimer (-)-silvestrol was accompushed from D-glucose, naringenin, and methyl cinnamate (see scheme). The key steps of the sequence were inspired by the possible biogenesis of these compounds.

PROCESSES AND INTERMEDIATES

The present invention relates to synthetic processes for the preparation of compounds bearing a dioxanyl moiety, in particular to compounds bearing a dioxanyl side chain attached to a mono- or polycyclic core moiety, more particularly a cyclopentabenzofuran core moiety. The invention also relates to intermediate compounds used in these processes. Compounds which can be prepared by the process of the invention can be used as candidates for screening for potential therapeutic activity, thus the invention also relates to compounds obtainable or prepared by the methods described above, in particular to those having cytotoxic or cytostatic activity.

Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium

A facile method for enzymatic glycosylation of 4-substituted benzyl alcohols and tyrosol with glucose in a monophasic aqueous-dioxane medium was reported, using a crude meal of apple seed as a new catalyst. The corresponding β-D-glucosides were synthesized in moderate yields (13.1-23.1%), among which the salidroside was obtained in 15.8% yield.