Cellulose tris

Chiralcel OD Cellulose tris(3,5-dimetltylphenylcarbamate) coated on silica gel [11,19,67,68] Daicel, [67,68]... 

Starting from a collection of samples remarkably well resolved (alpha > 6) on Chiralcel OD (Cellulose tris(3,5-dimethylphenylcarbamate) coated on aminopropyl silica), a putative three-point enantiophore for binding to CSR was derived (Fig. 4-10). This enantiophore query was used to search (CFS 3D search) within a list comprising 4203 compounds tested on Chiralcel OD. From this search domain of CHIRBASE 3D, 191 structures were found to match the enantiophore. 

Chiralcel OD Cellulose tris(3,5-dimethylphenylcarbamate coated on amino-propyl silica. 

A precursor in the synthesis of a promising calcium sensitizing agent from E. Merck [33], a chiral thiadiazin-2-one EMD 53986, 3,6-Dihydro-5-[l,2,3,4-tetrahy-dro-6-quinolyl]-6-methyl-2H-l,3,4-thiadiazin-2-one [26]. The study was performed using Celluspher , a CSP prepared from cellulose tri(p-methylbenzoate) according to a patent from Ciba-Geigy [34]. The spherical particles had a mean particle diameter of 20 3 pm and the mobile phase was pure methanol. 

Chiralcel OJ Cellulose tris(4-methylbenzoate) coated on sihca gel [19] Daicel... 

Chankvetadze, B., Yamamoto, C., Tanaka, N., Nakanishi, K., Okamoto, Y. (2004). High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with cellulose tris(3,5-dimethylphenylcarbamate). J. Sep. Sci. 27, 905-911. 

Acetate A general name for processes for making cellulose acetate fibers. Cellulose is acetylated, dissolved in acetone, and spun into fibers by injecting through orifices into heated chambers. Cellulose mono-acetate is made by acetylating with a mixture of acetic acid, acetic anhydride, and sulfuric acid as the catalyst. Cellulose tri-acetate is made in a similar fashion, but using perchloric acid as the catalyst, and dry-spinning from a solution in ethanol/ methylene chloride. Cellulose tri-acetate fibers were first made commercially by Courtaulds in London in 1950. 

The chiral recognition ability of a CSP is quantitatively evaluated from the results of chromatographic separation of enantiomers. Figure 3.4 shows a chromatogram of the resolution of benzoin (19) on cellulose tris(3,5-dimethylphenylcarbamate). The (+)-isomer elutes first followed by the (—)-isomer complete baseline separation is achieved. The results of the separation can be expressed by three parameters—capacity factors (k1), separation factor (a), and resolution factor (Rs)—defined as follows ... 

Figure 3.4 Optical resolution of 19 on cellulose tris(3,5-dimethylphenylcarbamate) column 25 x 0.46 (i.d.) cm eluent hexane/2-propanol (90/10) flow rate 0.5 ml/min (i.d. = inside diameter).

Figure 3.33 Plots of retention times t of (a) acetone and (b) first enantiomer of 39 to elute on cellulose tris(phenylcarbamate) derivatives against Hammett parameter a of substituents. (Reprinted with permission from Ref. 130. Copyright 1986 by Elsevier Science.)...

These polysaccharide-based stationary phases appear to be the most useful in organic, bio-organic and pharmaceutical analysis. Of the above-mentioned derivatives three of them, namely cellulose tris-(3,5-dimethylphenylcarbamate), amylose tris-(3,5-dimethylphenylcarbamate) and cellulose tris-(4-methylbenzoate), have very complementary properties and numerous publications have demonstrated that they have been able to achieve the chiral resolution of more than 80% of the drugs currently available on the market. " These CSPs are known under the commercial names, Chiralcel OD-H , Chiralpak AD and Chiralcel OJ , respectively (Figure 4). Their very broad enantiorecognition range is also the... 

Hollosep High Rejection Type is characterized by Cellulose Tri Acetate (CTA) hollow fiber with dense membrane structure and high salt rejection, and also by the module configuration favorable for uniform flow of feed water through hollow fiber layers (5 ). These features suggest that Hollosep may be operated under the conditions of higher recovery ratio compared to conventional conditions. 

Preparation of Hollow Fiber Membrane. CTA (Cellulose Tri-Acetate) hollow fiber membranes were prepared by aplnning a dope solution of CTA followed by soaking and anealing. 

Figure 3.1 Chemical structures of the current most successfully employed derivatised polysaccharide CSPs. (a) CHIRALPAK AD Amylose tris (3,5-dimethylphenylcarbamate) coated onto a silica support, (b) CHIRALPAK AS Amylose tris [(S)-a-methylbenzylcarbamate] coated onto a silica support, (c) CHIRALCEL OD Cellulose tris (3,5-dimethylphenylcarbamate) coated onto a silica support, (d) CHIRALCEL OJ Cellulose tris (4-methylbenzoate) coated onto a silica support.

A single CSP cannot be used for the chiral resolution of all racemic compounds. Therefore, different CSPs were used for the chiral resolution of different racemates. To make this part easy and clear, Table 1 includes the names of 20 CSPs and their most frequent applications. However, some other interesting applications are possible. Upon screening about 510 racemic compounds described in the literature, we observed that 229 of them resolved completely and 86 partially on cellulose tris(3,5-dimethylphenylcarbamate), and the rest not at all. For amylose tris(3,5-dimethylphenylcarbamate) CSP, we screened 384 racemic compounds and observed that 107 resolved completely and 102 partially. Clearly, cellulose and amylose tris(3,5-diphenylcarbamate) CSPs have the ability to resolve about 80% of the racemic compounds investigated. 

Chiralcel OJ Cellulose tris(4-methyl benzoate) Aryl methyl esters, aryl methoxy esters ... 

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