Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides.
نویسندگان
چکیده
A new iterative one-pot sequential method for the solution-phase synthesis of oligosaccharides has been devised on the basis of the electrochemical oxidation of a propagating thioglycoside terminus to generate the corresponding triflate, followed by the reaction with a thioglycoside building block having a free hydroxyl group. A practical automated synthesizer was developed for the method and was effectively used for assembling up to six thioglycoside building blocks to synthesize partial structures of poly-β-D-(1-6)-N-acetylglucosamine.
منابع مشابه
1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides
1,3-Dibromo-5,5-dimethylhydantoin (DBDMH), an inexpensive, non-toxic and stable reagent, is a competent activator of thioglycosides for glycosidic bond formation. Excellent yields were obtained when triflic acid (TfOH) or trimethylsilyl trifluoromethanesulfonate (TMSOTf) were employed as co-promoters in solution or automated glycan assembly on solid phase.
متن کامل4-(pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation.
This study focusses on a new concept for oligosaccharide synthesis based on 4-(pyridin-2-yl)thiazol-2-yl thioglycosides that can either act as effective glycosyl donors or can be deactivated by stable bidentate complexation with palladium(II) bromide.
متن کامل2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis
The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of...
متن کاملTotal synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block
The total synthesis of TMG-chitotriomycin using an automated electrochemical synthesizer for the assembly of carbohydrate building blocks is demonstrated. We have successfully prepared a precursor of TMG-chitotriomycin, which is a structurally-pure tetrasaccharide with typical protecting groups, through the methodology of automated electrochemical solution-phase synthesis developed by us. The s...
متن کاملSynthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks
We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated sol...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic letters
دوره 15 17 شماره
صفحات -
تاریخ انتشار 2013