REACTIONS OF SUGAR CHLOROSULFATES: PART V. THE SYNTHESIS OF CHLORODEOXY SUGARS
The reaction of sulfuryl chloride with reducing sugars and their methyl glycopyranosides was shown to produce fully substituted pyranose derivatives containing both chlorodeoxy and chlorosulfate ester groups. It was demonstrated that the chlorodeoxy groups were formed by nucleophilic displacement (S...
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| Published in | Canadian journal of chemistry Vol. 43; no. 8; pp. 2372 - 2386 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Ottawa, Canada
NRC Research Press
01.08.1965
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| Online Access | Get full text |
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| Abstract | The reaction of sulfuryl chloride with reducing sugars and their methyl glycopyranosides was shown to produce fully substituted pyranose derivatives containing both chlorodeoxy and chlorosulfate ester groups. It was demonstrated that the chlorodeoxy groups were formed by nucleophilic displacement (S
N
2) by chloride ion of specific reactive chlorosulfate groups in fully chlorosulfated intermediates. The degree of chloro-substitution was shown to be determined by both steric and electronic effects in the individual pyranose derivatives. |
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| AbstractList | The reaction of sulfuryl chloride with reducing sugars and their methyl glycopyranosides was shown to produce fully substituted pyranose derivatives containing both chlorodeoxy and chlorosulfate ester groups. It was demonstrated that the chlorodeoxy groups were formed by nucleophilic displacement (S
N
2) by chloride ion of specific reactive chlorosulfate groups in fully chlorosulfated intermediates. The degree of chloro-substitution was shown to be determined by both steric and electronic effects in the individual pyranose derivatives. |
| Abstract_FL | non disponible |
| Author | Jones, J. K. N Jennings, H. J |
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| Cites_doi | 10.1139/v60-156 10.1021/ed032p344 10.1021/ja01200a037 10.1021/ja01340a056 10.1139/v63-163 10.1139/v62-216 10.1021/ja01143a011 10.1021/ja01653a029 10.1002/ange.19530652304 |
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| Title | REACTIONS OF SUGAR CHLOROSULFATES: PART V. THE SYNTHESIS OF CHLORODEOXY SUGARS |
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