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3 article(s) from Hurevich, Mattan

DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support

Johnny N. Naoum,
Koushik Chandra,
Dorit Shemesh,
R. Benny Gerber,
Chaim Gilon and
Mattan Hurevich

Beilstein J. Org. Chem. 2017, 13, 806–816, doi:10.3762/bjoc.13.81

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Figure 1: Collidine-assisted vs DMAP-assisted N-methylation process on solid support. (A) Collidine-assisted ...

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Figure 2: Motifs 1–5 were used as models for the optimization of the N-methylation process. i) Introduction o...

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Figure 3: Sulfonylation optimization study. HPLC trace overlay that shows the sulfonylation of motif 4 to yie...

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Figure 4: DFT calculations for the reaction of o-NBS-Cl with a) collidine and b) DMAP. The structure of the r...

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Figure 5: Methylation of motif 3a to 3b using various reaction conditions. HPLC trace overlay presents the ef...

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Figure 6: Optimization of o-NBS removal reaction conditions demonstrated on motif 5b. HPLC trace overlay of i...

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Figure 7: HPLC trace overlay and MS analysis of the somatostatin analogue, 1SW-1, which was N^α-methylated on ...

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Published 03 May 2017

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Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

Markus W. Weishaupt,
Stefan Matthies,
Mattan Hurevich,
Claney L. Pereira,
Heung Sik Hahm and
Peter H. Seeberger

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

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Figure 1: Disaccharide repeating unit of the S. pneumoniae serotype 3 CPS.

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Figure 2: Building blocks and solid support for the automated solid-phase synthesis of S. pneumoniae serotype...

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Scheme 1: Attempted assembly of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagent...

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Figure 3: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 5; conditions: YM...

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Scheme 2: Attempted AGA of SP3 trisaccharide 9 using glycosyl phosphate building blocks 1 and 3. Reagents and...

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Figure 4: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 9; conditions: YM...

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Scheme 3: Automated synthesis of linker-bound glucuronic acid 10 using glycosyl phosphate building block 1. R...

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Scheme 4: Automated synthesis of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagen...

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Figure 5: HPLC chromatogram of the crude products of the automated solid-phase SP3 trisaccharide 5 synthesis;...

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Scheme 5: Global deprotection of SP3 trisaccharide 5. Reagents and conditions: a) LiOH, H₂O₂, THF, −5 °C to r...

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Published 12 Jul 2016

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Automated synthesis of sialylated oligosaccharides

Davide Esposito,
Mattan Hurevich,
Bastien Castagner,
Cheng-Chung Wang and
Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

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Figure 1: (a) Synthesis sequence for the preparation of building blocks 4 and 5; (b) Retrosynthetic analysis ...

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Scheme 1: Reagents and conditions: (i) PhI(OAc)_2, BF₃·Et₂O, CH₂Cl_2, −40 °C; then Ac₂O, pyridine; (ii) N₂H₄·Ac...

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Scheme 2: Reagents and conditions. (i) TMSOTf, DCM, −10 °C, 80%; (ii) NaOMe, MeOH; then KOH, MeOH, 60 °C; the...

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Scheme 3: Automated synthesis of 20. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...

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Scheme 4: Automated synthesis of 16. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...

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Scheme 5: Automated synthesis of 27. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...

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Scheme 6: Automated synthesis of 30. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...

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Scheme 7: Reagents and conditions: (i) 10% DMF in PBS buffer pH 7.5, overnight, 80%.

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Published 21 Sep 2012

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