178425-80-4Relevant academic research and scientific papers
Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses
Lin, Hui-Chang,Wu, Hsu-Hsuan,Lin, Zi-Ping,Lin, Chih-Yuan,Lin, Chun-Hung,Chen, Kun-Lung,Wong, Fung Fuh
supporting information; experimental part, p. 7327 - 7329 (2010/02/28)
α-2-Deoxyglycosides were successfully synthesized by means of microwave-assisted glycosylation. Hex-1-en-3-uloses were treated with a catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under microwave conditions.
Synthesis of α-2-deoxyglycosides by acid-mediated conjugate addition
Mann, Brent,Pitts, Daniel,Koviach, Jennifer
, p. 161 - 168 (2007/10/03)
A new method for the synthesis of α-2-deoxyglycosides from hex-1-en-3-uloses is reported. Several acids were surveyed for their ability to mediate the conjugate addition of cyclohexanol to a glucal derived αβ-unsaturated ketone. Although several acids suc
MICHAEL-type additions in the synthesis of α-O- and -S-2-deoxyglycosides
Michael, Katja,Kessler, Horst
, p. 3453 - 3456 (2007/10/03)
O- and S-Nucleophiles including galactose, serine and cysteine derivatives undergo MICHAEL-type additions to hex-1-en-3-uloses to furnish stereoselectivity the α-2-deoxy-ulosides. The keto function at C-3 can be reduced stereoselectively with NaBH4. Both configurations can be obtained depending on the presence or absence of CeCl3. Glycosylation takes place either base catalyzed with DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or KCN/18-crown-6 or acid catalyzed by ZnI2.
