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Investigations of g...
Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors
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- Olsson, Johan D. M. (författare)
- Stockholms universitet,Institutionen för organisk kemi,Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
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- Eriksson, Lars (författare)
- Stockholm Univ, Div Struct Chem, S-10691 Stockholm, Sweden.
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- Lahmann, Martina (författare)
- Stockholms universitet,Institutionen för organisk kemi,Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
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- Oscarson, Stefan (författare)
- Stockholms universitet,Institutionen för organisk kemi,Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
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(creator_code:org_t)
- 2008-08-20
- 2008
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 73:18, s. 7181-7188
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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https://urn.kb.se/re...
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Abstract
Ämnesord
Stäng
- NIS/AgOTf-promoted glycosylations with ethyl 2,3-N,O-carbonyl-2-deoxy-1-thio-beta-D-glueopyranoside donors can be performed with either alpha- or beta-selectivity by tuning the reaction conditions. Small amounts of AgOTf (0.1 equiv) and short reaction times give beta-selectivity, whereas 0.4 equiv of AgOTf and prolonged reaction times afford alpha-linked products. NMR-monitored glycosylation and anomerization experiments show initial formation of exclusively the beta-linkage, which anomerizes, through an intramolecular mechanism involving an endocyclic C - O bond cleavage, to the alpha-linkage.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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- art (ämneskategori)
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