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Volumn 8, Issue 24, 2006, Pages 5617-5620

Synthesis of α-fluorosulfonate and α-fluorosulfonamide analogues of a sulfated carbohydrate

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; CARBOHYDRATE; ESTER; FLUORIDE; FLUOROSULFONIC ACID; LITHIUM BROMIDE; LITHIUM DERIVATIVE; OXYGEN; SULFATE; SULFURIC ACID; UNCLASSIFIED DRUG;

EID: 33846010139     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062357z     Document Type: Article
Times cited : (14)

References (26)
  • 20
    • 0029890891 scopus 로고    scopus 로고
    • We were unable to obtain the crystal structure of the monofluorinated diastereomers and therefore we were unable to determine their absolute stereochemistry, which makes rationalizing the effect of the counterion on the stereochemistry very difficult. In contrast to the significant number of theoretical and synthetic studies on α-carbanions of sulfones, studies related to α-carbanions of sulfonate esters and sulfonamides are scarce. As with the sulfones, many factors may affect their structure and reactivity patterns such as negative hyperconjugation, complexation of the cations with the sulfonate group or carbanion, π-cation and cation-solvent interactions, differences in the sizes of the cations, etc. For a discussion on the structure of α-carbanions of sulfones see: Raabe, G, Gais, H-J, Fleishhauer, J. J. Am. Chem. Soc. 1996, 118, 4622 and references therein
    • We were unable to obtain the crystal structure of the monofluorinated diastereomers and therefore we were unable to determine their absolute stereochemistry, which makes rationalizing the effect of the counterion on the stereochemistry very difficult. In contrast to the significant number of theoretical and synthetic studies on α-carbanions of sulfones, studies related to α-carbanions of sulfonate esters and sulfonamides are scarce. As with the sulfones, many factors may affect their structure and reactivity patterns such as negative hyperconjugation, complexation of the cations with the sulfonate group or carbanion, π-cation and cation-solvent interactions, differences in the sizes of the cations, etc. For a discussion on the structure of α-carbanions of sulfones see: Raabe, G.; Gais, H-J.; Fleishhauer, J. J. Am. Chem. Soc. 1996, 118, 4622 and references therein.
  • 23
    • 33846014416 scopus 로고    scopus 로고
    • See the Supporting Information for the synthesis of reagent 23
    • See the Supporting Information for the synthesis of reagent 23.
  • 24
    • 33845977125 scopus 로고    scopus 로고
    • We did not detect compound 16 as a byproduct in these reactions. However, 19F NMR analysis of the crude reaction products suggested a byproduct resulting from the attack of the carbanion on the sulfur of NFSi may have formed. This side reaction was shown to occur during the fluorination of other alkyl sulfonamides see ref 18
    • 19F NMR analysis of the crude reaction products suggested a byproduct resulting from the attack of the carbanion on the sulfur of NFSi may have formed. This side reaction was shown to occur during the fluorination of other alkyl sulfonamides (see ref 18).
  • 25
    • 85119737699 scopus 로고
    • (a) Eisleb, Chem. Ber. 1941, 74, 1433.
    • (1941) Chem. Ber , vol.74 , pp. 1433
    • Eisleb1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.