2004
DOI: 10.1002/ejoc.200400266
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Synthesis of Glycosyl Phosphonates by Michael‐Type Addition to 2‐Nitroglycals

Abstract: A new synthetic strategy, which allows to synthesize both α-and β-anomers of 2-acetylaminoglycosyl phosphonate or exclusively β-anomer is described. The present strategy is a successful Michael-type addition of dimethyl hydrogen phosphonate to 2-nitroglycals.

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Cited by 25 publications
(19 citation statements)
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“…[198] High stereoselectivity was also observed in the glycosylation of aromatic alcohols, including the tyrosine derivative 115 (Scheme 17 b). [203] Other nucleophiles, such as lactates, [204] resonance-stabilized soft carbanions, [205] and dimethyl hydrogen phosphonate, [206] were added to 2-nitroglycals in a stereoselective fashion to give the corresponding glycosyl lactates, C-glycosides, and glycosyl phosphonates, respectively, in very good yields. [204][205][206] This method has been applied to the synthesis of complex oligosaccharides.…”
Section: Angewandte Chemiementioning
confidence: 99%
See 1 more Smart Citation
“…[198] High stereoselectivity was also observed in the glycosylation of aromatic alcohols, including the tyrosine derivative 115 (Scheme 17 b). [203] Other nucleophiles, such as lactates, [204] resonance-stabilized soft carbanions, [205] and dimethyl hydrogen phosphonate, [206] were added to 2-nitroglycals in a stereoselective fashion to give the corresponding glycosyl lactates, C-glycosides, and glycosyl phosphonates, respectively, in very good yields. [204][205][206] This method has been applied to the synthesis of complex oligosaccharides.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…[203] Other nucleophiles, such as lactates, [204] resonance-stabilized soft carbanions, [205] and dimethyl hydrogen phosphonate, [206] were added to 2-nitroglycals in a stereoselective fashion to give the corresponding glycosyl lactates, C-glycosides, and glycosyl phosphonates, respectively, in very good yields. [204][205][206] This method has been applied to the synthesis of complex oligosaccharides. A range of complex glycals were synthesized by the glycosylation of simple glycals with trichloroacetimidate donors in the presence of the mild Lewis acid Sn(OTf) 2 and then exposed to the nitration conditions.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…Hohe Stereoselektivitäten wurden bei der Glycosylierung von aromatischen Alkoholen, einschließlich des Tyrosinderivats 115 (Schema ) beobachtet 203. Andere Nucleophile wie Lactate,204 resonanzstabilisierte weiche Carbanionen205 und Dimethylhydrogenphosphonate206 wurden mit 2‐Nitroglycalen ebenfalls in stereoselektiver Weise verknüpft; erhalten wurden entsprechende Glycosyllactate, C ‐Glycoside bzw. Glycosylphosphonate in hohen Ausbeuten 204–206…”
Section: Glycosyldonoren Und Aktivierungsbedingungenunclassified
“…Thus, we hypothesized that the formation of the thermodynamically more stable 1,2diequatorial 2-nitrophosphonate likely results from a ring opening/ring closure event (Scheme 2A), as observed previously. 33 We anticipated that the introduction of more rigidity by means of a (tBu) 2 Si protecting group creating a trans-fused bicyclic system would provide insight in the mechanism. The 5 H 4 conformer is unattainable in case of the 4,6-O-di-tert-butylsilylene protected glycal 1j, since the ring-fused bonds cannot adopt the axial positions.…”
mentioning
confidence: 99%