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1 article(s) from de Paz, José L.

Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

Teresa Mena-Barragán,
José L. de Paz and
Pedro M. Nieto

Beilstein J. Org. Chem. 2019, 15, 137–144, doi:10.3762/bjoc.15.14

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Graphical Abstract

Scheme 1: Retrosynthetic analysis for the preparation of CS oligosaccharides. Lev = levulinyl; Piv = pivaloyl...

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Scheme 2: Reagents and conditions: a) TMSOTf, CH₂Cl₂, 0 °C, 30 min, 97%; b) (HF)_n·Py, THF, 0 °C, 20 h, 90%; c...

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Scheme 3: Reagents and conditions: a) C₈F₁₇CH₂CH₂COCl, Et₃N, DMAP, DMF/CH₂Cl₂, 0 °C to rt, 6 h, 70%; b) Ac₂O,...

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Scheme 4: Reagents and conditions: a) TMSOTf, CH₂Cl₂, 0 °C, 30 min, 25% (14α) + 33% (14β).

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Scheme 5: Reagents and conditions: a) LiOH, H₂O₂, THF, −5 °C to rt, 24 h, then NaOH, MeOH, 72 h, then Ac₂O, Et...

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Scheme 6: Reagents and conditions: a) 2-propanol, TMSOTf, CH₂Cl₂, 0 °C, 30 min, 73%; b) NH₂NH₂·H₂O, Py/AcOH, ...

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Scheme 7: Reagents and conditions: a) NH₂NH₂·H₂O, Py/AcOH, CH₂Cl₂, 1 h, 55%; b) TMSOTf, CH₂Cl₂, 0 °C, 30 min,...

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Scheme 8: Reagents and conditions: a) 4-Methoxyphenol, TMSOTf, CH₂Cl₂, 0 °C, 50 min, 92%; b) NH₂NH₂·H₂O, Py/A...

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Published 15 Jan 2019

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