Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 95-104 |
| Number of pages | 10 |
| Journal | Carbohydrate Research |
| DOIs | |
| Publication status | Published - 1 Jan 2019 |
Fingerprint
Keywords
- Cleavable aglycon
- Glycosylation
- Janus aglycon
- Spacer aglycon
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
Cite this
Janus glycosides of next generation : Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides. / Stepanova, Elena V.; Abronina, Polina I.; Zinin, Alexander I.; Chizhov, Alexander O.; Kononov, Leonid O.
In: Carbohydrate Research, 01.01.2019, p. 95-104.Research output: Contribution to journal › Article
}
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
UR - http://www.scopus.com/inward/citedby.url?scp=85057463841&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2018.11.013
DO - 10.1016/j.carres.2018.11.013
M3 - Article
SP - 95
EP - 104
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -