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1 article(s) from Salta, Joana

Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and their evaluation as L-selectin inhibitors

Joana Salta,
Jens Dernedde and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2015, 11, 638–646, doi:10.3762/bjoc.11.72

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Scheme 1: General approach to divalent or trivalent carbohydrate mimetics on the basis of aminopyran 1 or ser...

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Scheme 2: Hydroxy group protection of aminopyran 1 to give compound 3, synthesis of amide 4 and subsequent de...

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Scheme 3: Attempt to synthesize protected divalent compound 6. Conditions: a) succinic acid dichloride, Et₃N,...

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Scheme 4: HATU-mediated synthesis of divalent amide 25 and trivalent amides 27 and 29. Conditions: a) HATU, Et...

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Scheme 5: Polysulfations of amides 5 and 13. Conditions: a) 1) SO₃∙DMF, DMF-d₇, 1 d, rt; 2) 1 M NaOH, 0 °C; 3...

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Scheme 6: Polysulfation of divalent amides 21 and 22 leading to tetrasulfated amides 32 and 33. Conditions: a...

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Scheme 7: Conversion of trivalent compound 27 into nonasulfated carbohydrate mimetic 34. Conditions: a) 1) SO₃...

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Figure 1: Structures of O-sulfated divalent amide 32 and trivalent amide 34 and their respective IC₅₀ values ...

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Published 05 May 2015

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