Cadmium Carbonate


[513-78-0]  · CCdO3  · Cadmium Carbonate  · (MW 172.42)

(used in the preparation of aryl glycosides1-8 and also for cleavage of thioacetals9)

Physical Data: mp 357 °C; d 4.258 g cm-3.

Solubility: sol concentrated ammonia and dilute acids.

Form Supplied in: white powder and chunks.

Handling, Storage, and Precautions: should be stored in a cool dry place. It is a carcinogen and hence should be handled carefully.

Synthesis of Glycosides.

CdCO3 has been used as a catalyst in the Koenigs-Knorr synthesis of aryl glycosides.1-3 Better yields are reported with CdCO3 than with the usual catalyst, silver carbonate. For example, the 3-b-D-glucuronide triacetate methyl ester of estrone was prepared in 71% yield (eq 1), compared to 7% yield using silver carbonate.1 Similar preparations of the b-D-glucuronides of 17b-estradiol,1 estriol,1,4 equilin,1 equilenin,1 phenolphthalein,5 cholesterol,6 and anthracyclines7 are documented in the literature.

This methodology has also been used to prepare 2-aminoethyl glycosides (eq 2) for the preparation of carbohydrate-protein conjugates.8

Cleavage of Thioacetals.

Thioacetals of aldosugars are cleaved by CdCO3 in the presence of HgCl2 (see Mercury(II) Chloride-Cadmium Carbonate). This method has been used to prepare acyclic derivatives of monosaccharides (eq 3).9

1. (a) Conrow, R. B.; Bernstein, S. JOC 1971, 36, 863. (b) Fieser, M.; Fieser, L. F. FF 1974, 4, 67.
2. Dick, W. E. Carbohydr. Res. 1979, 70, 313.
3. Wallace, J. E.; Schroeder, L. R. JCS(P1) 1976, 1938.
4. Shimada, K.; Xie, F.; Nambara, T. CPB 1986, 34, 179.
5. Nambara, T.; Takizawa, N.; Goto, J.; Shimada, K. CPB 1976, 24, 2869.
6. Goto, J.; Suzaki, K.; Nambara, T. CPB 1979, 27, 1926.
7. Lown, J. W.; Sondhi, S, M.; Mandal, S. B.; Murphy, J. JOC 1982, 47, 4304.
8. King, R. R.; Cooper, F. P.; Bishop, C. Carbohydr. Res. 1977, 55, 83.
9. (a) Wolfrom, M. L. JACS 1929, 51, 2188. (b) Wolfrom, M. L. JACS 1930, 52, 2464. (c) Wolfrom, M. L.; Newlin, M. R.; Stahly, E. E. JACS 1931, 53, 4379. (d) Wolfrom, M. L.; Weisblat, D. I.; Zophy, W. H.; Waisbrot, S. W. JACS 1941, 63, 201.

Prabu Prabhakaran

Bristol-Myers Squibb Pharmaceutical Research Institute, New Brunswick, NJ, USA

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