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2 article(s) from Zamyatina, Alla

Approaches to stereoselective 1,1'-glycosylation

Daniele Zucchetta and
Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

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Scheme 1: Application of chloride-, bromide-, and trichloroacetimidate donors in 1,1'-coupling reactions towa...

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Scheme 2: Application of trichloroacetimidates as donors in 1,1'-β,α coupling reactions and the use of 1,2-or...

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Scheme 3: The β-anomeric configuration in the lactol acceptors can be trapped and fixed within the five-membe...

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Scheme 4: Diarylborinic acid-promoted β,α-1,1' glycosylation.

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Scheme 5: The anomeric configuration in the lactol acceptor can be trapped in the form of a TMS-glycoside.

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Scheme 6: The anomeric configuration in the lactol acceptor can be trapped in form of a 1-O-TMS-glycoside tha...

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Scheme 7: Influence of remote protecting groups on the stereoselectivity and efficiency of 1,1'-β,α bond form...

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Scheme 8: Synthesis of non-symmetrically fully orthogonally protected β,α-1,1' diglucosamines.

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Scheme 9: Synthesis of non-symmetric β,β-1,1'-linked disaccharides.

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Scheme 10: Synthesis of non-symmetric, fully orthogonally protected β,β-1,1'-diglucosamines.

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Scheme 11: Synthesis of α,α-1,1'-disaccharides.

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Scheme 12: Synthesis of α,α-1,1'-thiodisacchrides.

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Scheme 13: Synthesis of partially desymmetrized α,α-1,1'-linked disaccharides.

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Scheme 14: Synthesis of non-symmetric orthogonally protected α,α-1,1'-linked disaccharides involving an aminos...

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Review

Published 27 Aug 2025

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Aminosugar-based immunomodulator lipid A: synthetic approaches

Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

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Figure 1: (A) Gram-negative bacterial membrane with LPS as major component of the outer membrane; (B) structu...

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Figure 2: Structures of representative TLR4 ligands: TLR4 agonists (E. coli lipid A, N. meningitidis lipid A ...

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Figure 3: (A) Co-crystal structure of the homodimeric E. coli Ra-LPS·hMD-2∙TLR4 complex (PDB code: 3FXI); (B)...

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Figure 4: Co-crystal structures of (A) hybrid TLR4·hMD-2 with the bound antagonist eritoran (PDB: 2Z65, TLR4 ...

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Scheme 1: Synthesis of E. coli and S. typhimurium lipid A and analogues with shorter acyl chains.

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Scheme 2: Synthesis of N. meningitidis Kdo-lipid A.

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Scheme 3: Synthesis of fluorescently labeled E. coli lipid A.

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Scheme 4: Synthesis of H. pylori lipid A and Kdo-lipid A.

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Scheme 5: Synthesis of tetraacylated lipid A corresponding to P. gingivalis LPS.

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Scheme 6: Synthesis of pentaacylated P. gingivalis lipid A.

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Scheme 7: Synthesis of monophosphoryl lipid A (MPLA) and analogues.

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Scheme 8: Synthesis of tetraacylated Rhizobium lipid A containing aminogluconate moiety.

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Scheme 9: Synthesis of pentaacylated Rhizobium lipid A and its analogue containing ether chain.

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Scheme 10: Synthesis of pentaacylated Rhizobium lipid A containing 27-hydroxyoctacosanoate lipid chain.

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Scheme 11: Synthesis of zwitterionic 1,1′-glycosyl phosphodiester: a partial structure of GalN-modified Franci...

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Scheme 12: Synthesis of a binary 1,1′-glycosyl phosphodiester: a partial structure of β-L-Ara4N-modified Burkh...

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Scheme 13: Synthesis of Burkholderia lipid A containing binary glycosyl phosphodiester linked β-L-Ara4N.

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Review

Published 04 Jan 2018

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