Intramolecular cyclization of pentose and hexose dithioacetals

作者: Karl Blumberg , Anthony Fuccello , Theodorus van Es

DOI: 10.1016/S0008-6215(00)87102-5

关键词: Intramolecular cyclizationChemistryIdoseRiboseMedicinal chemistryHexoseTosylPentoseOrganic chemistry

摘要: Abstract The intramolecular cyclization of O -tosyl derivatives dithioacetals d -ribose, -arabinose, and -glucose was investigated. p -Toluenesulfonylation diethyl dithioacetal gave 3,6-anhydro- dithioacetal. Variously substituted 5- -tosyl- dibenzyl either 2,5-anhydro- l -idose dithioacetal, benzyl 1,5-dithio- -idopyranoside, or Likewise, 4- 1,4-dithio- -galactofuranoside derivatives.

参考文章(23)
J. Defaye, 2,5-Anhydrides of Sugars and Related Compounds Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 25, pp. 181- 228 ,(1970) , 10.1016/S0065-2318(08)60428-X
D. Horton, J.D. Wander, Conformation of acyclic derivatives of sugars. Carbohydrate Research. ,vol. 10, pp. 279- 288 ,(1969) , 10.1016/S0008-6215(00)80469-3
Joseph D. Wander, Derek Horton, Dithioacetals of Sugars Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 32, pp. 15- 123 ,(1976) , 10.1016/S0065-2318(08)60336-4
Theodorus van Es, p-Toluenesulfonylation of O-methyl derivatives of D-xylose dialkyl dithioacetals Carbohydrate Research. ,vol. 37, pp. 373- 380 ,(1974) , 10.1016/S0008-6215(00)82928-6
D. T. Williams, J. K. N. Jones, THE SEPARATION OF ALDOPENTOSE AND ALDOHEXOSE DIETHYL DITHIOACETAL DERIVATIVES BY GAS–LIQUID PARTITION CHROMATOGRAPHY Canadian Journal of Chemistry. ,vol. 44, pp. 412- 415 ,(1966) , 10.1139/V66-055
Helmut Zinner, Gerhard Rembarz, Hans-Peter Klöcking, Derivate der Zucker-mercaptale, VIII. Isopropylidenverbindungen derD-Arabinose-Mercaptale Chemische Berichte. ,vol. 90, pp. 2688- 2696 ,(1957) , 10.1002/CBER.19570901140
Robert E. Gramera, Trimbak R. Ingle, Roy L. Whistler, Elimination of the Exocyclic Secondary p-Tolylsulfonyloxy Group in a D-Glucofuranose Structure1,2 Journal of Organic Chemistry. ,vol. 29, pp. 878- 880 ,(1964) , 10.1021/JO01027A027
Helmut Zinner, Zur Identifizierung und Isolierung der Aldosen als Mercaptale Chemische Berichte. ,vol. 84, pp. 780- 784 ,(1951) , 10.1002/CBER.19510840815
M.A. Miljković, E.A. Davidson, An improved synthesis of 1,2-O-isopropylidene-β-l-idofuranose Carbohydrate Research. ,vol. 13, pp. 444- 446 ,(1970) , 10.1016/S0008-6215(00)80602-3