4196-36-5

Usage

Uses

Used in Organic Synthesis:
2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)hexopyranose is used as a key intermediate in organic synthesis for the development of complex organic molecules. Its lipophilic nature and unique structure facilitate the synthesis of various organic compounds with potential applications in different industries.
Used in Drug Development:
In the pharmaceutical industry, 2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)hexopyranose is used as a building block for the creation of drugs with lipophilic properties. Its high affinity for lipid molecules allows for the development of drugs that can effectively target and interact with biological membranes and other lipid-rich environments within the body, potentially leading to improved drug delivery and efficacy.
Used in Biological Research:
2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)hexopyranose is employed as a research tool in biological studies to investigate the interactions between lipophilic molecules and biological systems. Its unique structure allows researchers to gain insights into the behavior of lipophilic compounds within biological environments, which can contribute to a better understanding of their potential applications and effects on living organisms.
Used in Drug Delivery Systems:
In the field of drug delivery, 2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)hexopyranose is utilized as a component in the design of novel drug delivery systems. Its lipophilic properties can enhance the solubility and bioavailability of drugs, improving their therapeutic outcomes. Furthermore, its incorporation into drug delivery systems can help overcome limitations associated with traditional drug administration methods, such as poor absorption or rapid degradation.

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 693-13-0 diisopropyl-carbodiimide 
• 62-23-7 4-nitro-benzoic acid 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 93414-72-3 (1R)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-C-(2-thienyl)-D-glucitol 
• 93414-73-4 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-methoxyphenyl)-β-D-glucopyranose 
• 81972-19-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 
• 82659-52-7 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene 
• 201593-55-7 5,5-Dimethyl-2-thioxo-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-1,3,2-dioxaphosphorinane 
• 201593-51-3 5,5-Dimethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylsulfanyl)-[1,3,2]dioxaphosphinane 2-oxide 
• 73508-41-5 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-{hydroxy-[(R)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-phosphoryloxy}-ethyl ester 
• 73485-56-0 1-O-allyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-pivaloyl-sn-glycerol 
• 73485-57-1 1-O-pivaloyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-O-allyl-sn-glycerol 
• 73485-66-2 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(S)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 73485-66-2 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-hydroxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 73485-64-0 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(S)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 73485-64-0 Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[[(R)-3-[((E)-propenyl)oxy]-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propoxy]-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 78120-17-9 (R)-3-Allyloxy-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propan-1-ol 

Relevant academic research and scientific papers

Combined Lewis acid and Br?nsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Br?nsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein.

SYNTHESES OF 1-O-ACYLALDOSE DERIVATIVES via THE CORRESPONDING O-GLYCOSYLPSEUDOUREAS

A series of 1-O-acylaldose derivatives was prepared in good yield throught the reaction of 1,3-dialkyl-O-glycosylpseudoureas with carboxylic acids.