An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives
Апстракт
The aim of this work was to synthesize 2-deoxy-2-iodo-manno sugars and 2-deoxy-2-iodo manno esters of a satisfactory purity in the highest possible yield. For this put-pose, the iodination reaction of D-glucal triacetate (1), 3,4-di-O-acetyl-6-O-to-syl-D-glucal (2) and 3,4-di-O-acetyl-6-S-acetyl-6-thio-D-glucal (3) were investigated using a mixture of NaIO4-NaI at pH 6 (acetate buffer) and pH 7 (phosphate buffer) in a tert-butanol-water solvent system. Depending on the buffer system used, a mixture of the 2-deoxy-2-iodo-manno esters 4, 6 or 8 together with corresponding 2-deoxy-2-iodo sugars 5, 7, or 9 were obtained, or separately.
Кључне речи:
2-deoxy-2-iodo-manno-sugars / iodination D-glucal derivatives / modified synthesisИзвор:
Journal of the Serbian Chemical Society, 1998, 63, 9, 685-688Колекције
Институција/група
VinčaTY - JOUR AU - Djurendic, E AU - Vukojevic, N AU - Dramićanin, Tatjana AU - Canadi, J AU - Miljkovic, D PY - 1998 UR - https://vinar.vin.bg.ac.rs/handle/123456789/2190 AB - The aim of this work was to synthesize 2-deoxy-2-iodo-manno sugars and 2-deoxy-2-iodo manno esters of a satisfactory purity in the highest possible yield. For this put-pose, the iodination reaction of D-glucal triacetate (1), 3,4-di-O-acetyl-6-O-to-syl-D-glucal (2) and 3,4-di-O-acetyl-6-S-acetyl-6-thio-D-glucal (3) were investigated using a mixture of NaIO4-NaI at pH 6 (acetate buffer) and pH 7 (phosphate buffer) in a tert-butanol-water solvent system. Depending on the buffer system used, a mixture of the 2-deoxy-2-iodo-manno esters 4, 6 or 8 together with corresponding 2-deoxy-2-iodo sugars 5, 7, or 9 were obtained, or separately. T2 - Journal of the Serbian Chemical Society T1 - An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives VL - 63 IS - 9 SP - 685 EP - 688 UR - https://hdl.handle.net/21.15107/rcub_vinar_2190 ER -
@article{ author = "Djurendic, E and Vukojevic, N and Dramićanin, Tatjana and Canadi, J and Miljkovic, D", year = "1998", abstract = "The aim of this work was to synthesize 2-deoxy-2-iodo-manno sugars and 2-deoxy-2-iodo manno esters of a satisfactory purity in the highest possible yield. For this put-pose, the iodination reaction of D-glucal triacetate (1), 3,4-di-O-acetyl-6-O-to-syl-D-glucal (2) and 3,4-di-O-acetyl-6-S-acetyl-6-thio-D-glucal (3) were investigated using a mixture of NaIO4-NaI at pH 6 (acetate buffer) and pH 7 (phosphate buffer) in a tert-butanol-water solvent system. Depending on the buffer system used, a mixture of the 2-deoxy-2-iodo-manno esters 4, 6 or 8 together with corresponding 2-deoxy-2-iodo sugars 5, 7, or 9 were obtained, or separately.", journal = "Journal of the Serbian Chemical Society", title = "An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives", volume = "63", number = "9", pages = "685-688", url = "https://hdl.handle.net/21.15107/rcub_vinar_2190" }
Djurendic, E., Vukojevic, N., Dramićanin, T., Canadi, J.,& Miljkovic, D.. (1998). An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives. in Journal of the Serbian Chemical Society, 63(9), 685-688. https://hdl.handle.net/21.15107/rcub_vinar_2190
Djurendic E, Vukojevic N, Dramićanin T, Canadi J, Miljkovic D. An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives. in Journal of the Serbian Chemical Society. 1998;63(9):685-688. https://hdl.handle.net/21.15107/rcub_vinar_2190 .
Djurendic, E, Vukojevic, N, Dramićanin, Tatjana, Canadi, J, Miljkovic, D, "An improved synthesis for obtaining 2-deoxy-2-iodo-D-mannopyranose derivatives" in Journal of the Serbian Chemical Society, 63, no. 9 (1998):685-688, https://hdl.handle.net/21.15107/rcub_vinar_2190 .