Cellulose trisphenylcarbamate

Okamoto, Y., Kawashima, M., and Hatada, K. (1986) Controlled chiral recognition of cellulose trisphenylcarbamate derivatives supported on silica gel, J. Chromatogr. 363, 173-186. 

Yashima, E., Yamada, M., Kaida, Y., and Okamoto, Y. Computational studies on chiral discrimination mechanism of cellulose trisphenylcarbamate, J. Chromatogr. A 694, 347-354. 

Yashima, E.,Yamada,Y., Kaida,Y., Okamoto, Y, Computational Studies on Chiral Discrimination Mechanism on Cellulose Trisphenylcarbamate,... 

Figures. Top Schematic of cellulose trisphenylcarbamate octamer. Sampling was done within the enclosed box. Bottom Cubic sampling box of dimension r and mesh size r in A. Analyte is rotated in 60° increments about x, y and z axes at each grid point. Reproduced with permission from ref. 49.

Fig. 13 Cellulose trisphenylcarbamate derivatives. Printed by permission from Chemical Society of Japan [5]...

In 1984, we also reported that cellulose trisphenylcarbamate (31a in Fig. 13) coated on silica gel shows an excellent chiral recognition for many racemates and affords a... 

The possible molecular structures of cellulose trisphenylcarbamate 31a, its 3,5-dimethyl derivative 31x, and amylose tris(3,5-dimethylphenylcarbamate) 32 are shown in Fig. 18. Both cellulose derivatives have left-handed 3/2 helical structures [55], whereas the amylose derivative has a left-handed 4/3 helical structure [56]. The stmcture of cellulose tris(3,5-dimethylphenylcarbamate) 31x is clearly different firom that of 31a. The high chiral recognition of 31x is ascribed to the two methyl groups. In addition to the steric effect of the two methyl groups, their electron-donating effect can influence the polarity of the carbamate residue, which may allow the derivative to have a stiffer helical structure. The derivatives... 

Fig. 18 Molecular structures of (a) cellulose trisphenylcarbamate (31a), (b) cellulose tris (3,5-dimethylphenylcarbamate) (31x), and (c) amylose tris(3,5-dimethylphenylcarbamate) (32). Printed with permission of Chemical Society of Japan (a, b) [56] and American Chemical Society (c) [57]...

The cellulose derivatives used for chiral TLC are trisphenylcarbamate, 2,3-dichlorophenylcarbamate, 2,4 -dichlorophenylcarbamate, 2,6 -dichlorophenylcar-bamate, 3,4-dichlorophenylcarbamate, 3,5-dichlorophenylcarbamate, 2,3-dimethyl-phenylcarbamate, and 3,5-dimethylphenylcarbamate. Aboul-Enein et al. [178] have reviewed the chiral resolution of racemates on polysaccharide chiral TLC plates. They discussed the role of the substituents of polysaccharide derivatives on chiral resolution. The effects of the substituents of cellulose derivatives and the mechanisms of chiral resolution on these plates are similar to what is found for HPLC CSPs. 

Yashima E, Yamada M, Yamamoto C, Nakashima M, Okamoto Y (1997) Chromatographic enantioseparation and chiral discrimination in NMR by trisphenylcarbamate derivatives of cellulose, amylose, oligosaccharides, and cyclodextrins. Enantiomer 2 225-240... 

In 1997, Suedee and Heard [36] proposed the use of various cellulose triphenyl-carbamate derivatives to separate some enantiomeric j8-blockers on noncommercial plates. Cellulose derivatives tested are as follows (a) trisphenylcarbamate, (b) fm(2,3-dichlorophenyl)carbamate, (c) fra(2,4-dichlorophenyl)carbamate, (d) fm(2,6-dichlorophenyl)carbamate, (e) fm(2,3-dimethylphenyl)carbamate, (f) fra(3,4-dichlorophenyl)carbamate, (g) tris(3,5-dichlorophenyl)carbamate, and (h) fm(3,5-dimethylphenyl)carbamate. 

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