83058-25-7

Usage

Uses

Used in Organic Synthesis:
D-Cellotetraosetetradecaactetate is used as a synthetic intermediate for the preparation of various complex carbohydrates and their derivatives. Its unique structure and multiple acetate groups make it a versatile building block for the synthesis of oligosaccharides, glycoconjugates, and other bioactive molecules with potential applications in pharmaceuticals, diagnostics, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, D-Cellotetraosetetradecaactetate is used as a key component in the development of glyco-based drugs and vaccines. Its ability to mimic natural glycans and modulate immune responses makes it a promising candidate for the design of novel therapeutic agents targeting infectious diseases, autoimmune disorders, and cancers.
Used in Diagnostics:
D-Cellotetraosetetradecaactetate is employed as a diagnostic tool in the detection and identification of carbohydrate-binding proteins, such as lectins and antibodies. Its unique structural features allow for the development of sensitive and specific assays for the analysis of glycan-protein interactions, which are crucial for understanding the role of carbohydrates in various biological processes and diseases.
Used in Materials Science:
In materials science, D-Cellotetraosetetradecaactetate is utilized as a functional component in the fabrication of carbohydrate-based materials, such as hydrogels, nanoparticles, and thin films. Its ability to form stable and well-defined structures through self-assembly and cross-linking reactions enables the creation of advanced materials with tailored properties for applications in drug delivery, tissue engineering, and biosensing.

Upstream product

• 108-24-7 acetic anhydride 
• 69429-16-9 α-cellotetraose 

Relevant academic research and scientific papers

Studies of the series of cellooligosaccharide peracetates as a model for cellulose triacetate by 13C CP/MAS NMR spectroscopy and X-ray analyses

The series of crystalline oligomers from α-cellobiose octaacetate through α-cellohexaose eicosaacetate, listed as below, was prepared from homogeneous acetylation of the corresponding cellooligosaccharides and characterized by 13C CP/MAS NMR spectroscopy and X-ray analysis in order to obtain the structural models of cellulose triacetate (CTA) in solid state. Progressing toward the hexamer, the NMR spectral feature of the oligomers, in comparison with two allomorphs of CTA I and CTA II, gradually approached that of CTA I. Specifically, chemical shifts of both the hexamer and the pentamer were in considerable respective agreement with those of CTA I. In addition, X-ray diffraction patterns of the oligomers established that the crystalline pentamer and hexamer have a CTA I lattice in spite of recrystallization from ethylacetate-hexane. We therefore concluded that the pentamer and hexamer would be useful models for the CTA I structure. Copyright (C) 1999 Elsevier Science Ltd.

Oligosaccharide analogues of polysaccharides. Part 19. Synthesis of 2- (naphthalen-1-yl)ethyl cellooligoglycosides and [(naphthalene-1,8- diyl)di(ethane-2,1-diyl)] bis[cellooligoglycosides]

Glucosyl, cellobiosyl, cellotriosyl, cellotetraosyl, and cellooctaosyl residues were attached to naphthalene-1,8-diethanol (3) with the goal of preparing mimics of cellulose I. Among the templates that were considered, 1,8-diethynylnaphthalene (1) led to unstable products, and glycosidation of naphthalene-1,8-dimethanol (2) gave orthoesters that could not be rearranged to glycosides (Scheme 1). The conformation of 3 in the crystal and of its dimethyl ether 14 in solution was studied by X-ray analysis and force-field calculation (Figs. 1-3). Rotation around the Ar-CH2 and CH2-CH2 bonds of 14 is only weakly hindered and the O···O distance of crystalline 3 (6.01 A) corresponds to the mean distance of the parallel chains of cellulose I(β). The acetylated glycosyl bromides 18 and 19 were prepared by a new convergent synthesis (Scheme 2). Glycosylation of 3 by the glycosyl bromides 15-19 under established conditions of the Koenigs-Knorr reaction proved problematic, particularly on account of an acetyl transfer blocking one of the hydroxyethyl groups. Basic zinc carbonate, however, promoted glycosylation of 12 and 3 by the glycosyl bromides 15-19 and did not lead to transacetylation (Scheme 3). The mono- to tetrasaccharides 32-35 and 42-45 were isolated in yields of 5682%, and the octasaccharides 36 and 46 in 32 and 16%, respectively. The mono- and disaccharides 32, 33, 42, and 43 were deacetylated with NaOMe in MeOH. Aqueous NaOH was used for the tri-, tetra-, and octasaccharides 34-36 and 44-46, as their partially deacetylated derivatives proved insoluble in MeOH. The fully deprotected saccharides 37-41 and 47-50 were isolated in over 90%, while the yield of the dioctaoside 51 was lower on account of its poor water solubility.

First synthesis of cellooctaose by a convergent synthetic method

The first chemical synthesis of cellooctaose by a convergent synthetic method is described. A challenging glycosylation between cellotetraosyl donor 5 and acceptor 7 proceeded in a one-step reaction using a high-vacuum system for anhydrous glycosylation a