Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8233-8236

  Kartha, K P Ravindranathan ^a   Field, Robert A ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; GLYCOSIDE; IODINE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL ANALYSIS; GLYCOSYLATION; SYNTHESIS;

EID: 0030703549     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4039(97)10124-1     Document Type: Article

References (27)

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2. For reviews of the preparation and use of glycosyl halides and thioglycosides see: Modern Methods in Carbohydrate Synthesis; Khan, S.H.; O'Neill, R.A.; Eds.; Harwood Academic Publishers, 1996.
3. See reference 2, Norberg, T. Chapter 4, pp 82-106.
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24. 18
25. Schenkman, S.; Eichinger, D.; Pereira, M.E.A.; Nussenzweig, V.; Ann. Rev. Microbiol., 1994, 48, 499.
26. A typical glycosylation procedure involved addition of IBr (1.2 mol equiv.) to an ice-cold solution of the donor (1.2 mol equiv.) and acceptor in acetonitrile (4ml / mmol donor) containing 4Å molecular sieves +/-base (DABCO - 0.25 mol equiv.). The reaction was monitored by t.l.c., and was allowed to slowly warm to room temperature if it proved sluggish. On completion, the reaction mixture was diluted with dichloromethane, solids were removed by filtration and the dichloromethane solution was subjected to a standard work-up. Column chromatography gave the desired disaccharides (23) to (26), all of which gave spectroscopic and analytical data consistent with their proposed structures. Full details of the synthesis and biological evaluation of these and related compounds will be published in due course.
27. Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T.; Tetrahedron Lett., 1994, 35, 3979.