Reaction of glycosyl chlorides with silver perchlorate
| ISSN: |
0008-6215
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|---|---|
| Source: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
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| Topics: |
Chemistry and Pharmacology
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| Type of Medium: |
Electronic Resource
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| URL: |
| _version_ | 1798292393441624066 |
|---|---|
| autor | Igarashi, K. Honma, T. Irisawa, J. |
| autorsonst | Igarashi, K. Honma, T. Irisawa, J. |
| book_url | http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80449-8 |
| datenlieferant | nat_lic_papers |
| fussnote | When 3,4,6-tri-O-acetyl-2-chloro-2-deoxy-D-gluco-and-manno-pyranosyl chlorides were treated with silver perchlorate in anhydrous toluene, ether, or liquid sulfur dioxide, the corresponding α-D-glycosyl perchlorate esters were obtained. Methanolysis of the perchlorate (6) having the D-gluco configuration gave a mixture of the methyl α- and β-D-glucopyranosides, the proportion of which varied with the conditions. Treatment of 6 with tetraethylammonium chloride gave predominantly the β-D-glucopyranosyl chloride. Methanolysis or treatment with tetraethylammonium chloride of the perchlorate (7) having the D-manno configuration gave preponderantly the methyl α-D-mannopyranoside and the α-D-mannopyranosyl chloride, respectively.1,2-O-Acetoxonium-3,4,6-tri-O-acetyl-αD-glucopyranose perchlorate (13) was obtained in the reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride with silver perchlorate. Treatment of 13 with tetraethylammonium chloride gave 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride in good yield. The proportion of the methyl α- and β-D-glucopyranosides obtained by methanolysis of 13 was solvent dependent. |
| hauptsatz | hsatz_simple |
| identnr | NLZ175422591 |
| issn | 0008-6215 |
| journal_name | Carbohydrate Research |
| materialart | 1 |
| package_name | Elsevier |
| publikationsort | Amsterdam |
| publisher | Elsevier |
| reference | 15 (1970), S. 329-337 |
| search_space | articles |
| shingle_author_1 | Igarashi, K. Honma, T. Irisawa, J. |
| shingle_author_2 | Igarashi, K. Honma, T. Irisawa, J. |
| shingle_author_3 | Igarashi, K. Honma, T. Irisawa, J. |
| shingle_author_4 | Igarashi, K. Honma, T. Irisawa, J. |
| shingle_catch_all_1 | Igarashi, K. Honma, T. Irisawa, J. Reaction of glycosyl chlorides with silver perchlorate 0008-6215 00086215 Elsevier |
| shingle_catch_all_2 | Igarashi, K. Honma, T. Irisawa, J. Reaction of glycosyl chlorides with silver perchlorate 0008-6215 00086215 Elsevier |
| shingle_catch_all_3 | Igarashi, K. Honma, T. Irisawa, J. Reaction of glycosyl chlorides with silver perchlorate 0008-6215 00086215 Elsevier |
| shingle_catch_all_4 | Igarashi, K. Honma, T. Irisawa, J. Reaction of glycosyl chlorides with silver perchlorate 0008-6215 00086215 Elsevier |
| shingle_title_1 | Reaction of glycosyl chlorides with silver perchlorate |
| shingle_title_2 | Reaction of glycosyl chlorides with silver perchlorate |
| shingle_title_3 | Reaction of glycosyl chlorides with silver perchlorate |
| shingle_title_4 | Reaction of glycosyl chlorides with silver perchlorate |
| sigel_instance_filter | dkfz geomar wilbert ipn albert fhp |
| source_archive | Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
| timestamp | 2024-05-06T08:47:47.467Z |
| titel | Reaction of glycosyl chlorides with silver perchlorate |
| titel_suche | Reaction of glycosyl chlorides with silver perchlorate When 3,4,6-tri-O-acetyl-2-chloro-2-deoxy-D-gluco-and-manno-pyranosyl chlorides were treated with silver perchlorate in anhydrous toluene, ether, or liquid sulfur dioxide, the corresponding α-D-glycosyl perchlorate esters were obtained. Methanolysis of the perchlorate (6) having the D-gluco configuration gave a mixture of the methyl α- and β-D-glucopyranosides, the proportion of which varied with the conditions. Treatment of 6 with tetraethylammonium chloride gave predominantly the β-D-glucopyranosyl chloride. Methanolysis or treatment with tetraethylammonium chloride of the perchlorate (7) having the D-manno configuration gave preponderantly the methyl α-D-mannopyranoside and the α-D-mannopyranosyl chloride, respectively.1,2-O-Acetoxonium-3,4,6-tri-O-acetyl-αD-glucopyranose perchlorate (13) was obtained in the reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride with silver perchlorate. Treatment of 13 with tetraethylammonium chloride gave 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride in good yield. The proportion of the methyl α- and β-D-glucopyranosides obtained by methanolysis of 13 was solvent dependent. |
| topic | V |
| uid | nat_lic_papers_NLZ175422591 |