Safe and Alternate Process for the Reductions of Methanesulfonates: Application in the Synthesis of 1,2,3-Triacetyl-5-deoxy-d -ribofuranoside
| Autor: | Atchuta R. Parimi, Nagaraju Mekala, Murthy V. R. K. Moturu, Rao V. L. N. Dammalapati |
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| Rok vydání: | 2016 |
| Předmět: |
Commercial scale
010405 organic chemistry Organic Chemistry Diglyme 010402 general chemistry 01 natural sciences Diethylene glycol dimethyl ether 0104 chemical sciences chemistry.chemical_compound Sodium borohydride chemistry Anhydrous Organic chemistry Lithium chloride Physical and Theoretical Chemistry |
| Zdroj: | Organic Process Research & Development. 20:609-614 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/acs.oprd.5b00286 |
| Popis: | Diethylene glycol dimethyl ether, diglyme, and 1,2-bis(2-methoxyethoxy)ethane, triglyme, are found to be suitable and safe alternate solvents to DMSO for the reduction of methanesulfonate in sodium borohydride. Addition of anhydrous lithium chloride led to the complete reduction of methanesulfonate esters to the corresponding alkanes in the presence of sodium borohydride in these solvents (diglyme and triglyme). This protocol is useful in the preparation of 1,2,3-triacetyl-5-deoxy-d-ribofuranoside, 7, a key intermediate of Capecitabine, 1, on the commercial scale. |
| Databáze: | OpenAIRE |
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