TY - JOUR
T1 - Janus glycosides of next generation
T2 - Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides
AU - Stepanova, Elena V.
AU - Abronina, Polina I.
AU - Zinin, Alexander I.
AU - Chizhov, Alexander O.
AU - Kononov, Leonid O.
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Efficient procedures for the preparative synthesis of per-O-acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (D-glucose, D-galactose, D-mannose, L-rhamnose, D-arabinofuranose, D-glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could become next-generation Janus glycosides with cleavable spacer aglycon, ready for conjugation or further transformation.
AB - Efficient procedures for the preparative synthesis of per-O-acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (D-glucose, D-galactose, D-mannose, L-rhamnose, D-arabinofuranose, D-glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could become next-generation Janus glycosides with cleavable spacer aglycon, ready for conjugation or further transformation.
KW - Cleavable aglycon
KW - Glycosylation
KW - Janus aglycon
KW - Spacer aglycon
UR - http://www.scopus.com/inward/record.url?scp=85057463841&partnerID=8YFLogxK
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U2 - 10.1016/j.carres.2018.11.013
DO - 10.1016/j.carres.2018.11.013
M3 - Article
C2 - 30508661
AN - SCOPUS:85057463841
SP - 95
EP - 104
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -