Matches in SemOpenAlex for { <https://semopenalex.org/work/W2953182604> ?p ?o ?g. }
Showing items 1 to 69 of
69
with 100 items per page.
- W2953182604 abstract "The reaction of (E)-1-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(trimethylsiloxy)buta-1,3-diene 1 and maleic anhydride gives cycloadduct 10 and ketone 12. Reduction of ketone 13, formed by acidic hydrolysis of silyl enol ether 10, with sodium cyanoborohydride in acetic acid gives an 83 ∶ 17 mixture of the γ- and δ-lactone 14 and 15. γ-Lactone 14 is transformed into the aminomonocarba-disaccharide, 4-acetamido-2,4-dideoxy-3-O-(β-D-glucopyranosyl)-5a-carba-β-L-lyxo-hexopyranose 7, using a five-step procedure involving the Curtius rearrangement of acyl azide 16. A similar sequence using γ-lactone 21, prepared from ketone 12, gives the protected aminomonocarba-disaccharide, 4-acetamido-1,6-di-O-acetyl-2,4-dideoxy-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-5a-carba-β-D-lyxo-hexopyranose 8. Reaction of cycloadduct 10 with dimethyldioxirane gives acyloin 26. Acetylation under acidic conditions followed by reduction with sodium cyanoborohydride in acetic acid gives a 75 ∶ 25 mixture of the γ- and δ-lactone 28 and 29. Using a sequence similar to that employed for the preparation of compounds 7 and 8, γ-lactone 28 is converted into the fully substituted aminomonocarba-disaccharide, 4-acetamido-1,2,6-tri-O-acetyl-4-deoxy-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-5a-carba-β-L-galactopyranose 9." @default.
- W2953182604 created "2019-06-27" @default.
- W2953182604 creator A5024025035 @default.
- W2953182604 creator A5049507859 @default.
- W2953182604 creator A5070560132 @default.
- W2953182604 creator A5083837107 @default.
- W2953182604 date "2010-05-22" @default.
- W2953182604 modified "2023-09-24" @default.
- W2953182604 title "ChemInform Abstract: Studies Related to Carba-Pyranoses: A Strategy for the Synthesis of β-1,3-Glycosidically Linked Aminomonocarba-Disaccharides." @default.
- W2953182604 cites W2010565101 @default.
- W2953182604 doi "https://doi.org/10.1002/chin.200209197" @default.
- W2953182604 hasPublicationYear "2010" @default.
- W2953182604 type Work @default.
- W2953182604 sameAs 2953182604 @default.
- W2953182604 citedByCount "0" @default.
- W2953182604 crossrefType "journal-article" @default.
- W2953182604 hasAuthorship W2953182604A5024025035 @default.
- W2953182604 hasAuthorship W2953182604A5049507859 @default.
- W2953182604 hasAuthorship W2953182604A5070560132 @default.
- W2953182604 hasAuthorship W2953182604A5083837107 @default.
- W2953182604 hasConcept C161790260 @default.
- W2953182604 hasConcept C178790620 @default.
- W2953182604 hasConcept C185592680 @default.
- W2953182604 hasConcept C2776612806 @default.
- W2953182604 hasConcept C2776673659 @default.
- W2953182604 hasConcept C2777346074 @default.
- W2953182604 hasConcept C2777738585 @default.
- W2953182604 hasConcept C2779321498 @default.
- W2953182604 hasConcept C2779854550 @default.
- W2953182604 hasConcept C71240020 @default.
- W2953182604 hasConcept C94412978 @default.
- W2953182604 hasConceptScore W2953182604C161790260 @default.
- W2953182604 hasConceptScore W2953182604C178790620 @default.
- W2953182604 hasConceptScore W2953182604C185592680 @default.
- W2953182604 hasConceptScore W2953182604C2776612806 @default.
- W2953182604 hasConceptScore W2953182604C2776673659 @default.
- W2953182604 hasConceptScore W2953182604C2777346074 @default.
- W2953182604 hasConceptScore W2953182604C2777738585 @default.
- W2953182604 hasConceptScore W2953182604C2779321498 @default.
- W2953182604 hasConceptScore W2953182604C2779854550 @default.
- W2953182604 hasConceptScore W2953182604C71240020 @default.
- W2953182604 hasConceptScore W2953182604C94412978 @default.
- W2953182604 hasLocation W29531826041 @default.
- W2953182604 hasOpenAccess W2953182604 @default.
- W2953182604 hasPrimaryLocation W29531826041 @default.
- W2953182604 hasRelatedWork W1972004111 @default.
- W2953182604 hasRelatedWork W1972419139 @default.
- W2953182604 hasRelatedWork W1981175474 @default.
- W2953182604 hasRelatedWork W1983173151 @default.
- W2953182604 hasRelatedWork W2001257508 @default.
- W2953182604 hasRelatedWork W2004826632 @default.
- W2953182604 hasRelatedWork W2010565101 @default.
- W2953182604 hasRelatedWork W2013046391 @default.
- W2953182604 hasRelatedWork W2019543396 @default.
- W2953182604 hasRelatedWork W2020854728 @default.
- W2953182604 hasRelatedWork W2061728663 @default.
- W2953182604 hasRelatedWork W2062339721 @default.
- W2953182604 hasRelatedWork W2065574437 @default.
- W2953182604 hasRelatedWork W2067500972 @default.
- W2953182604 hasRelatedWork W2162020327 @default.
- W2953182604 hasRelatedWork W2173158620 @default.
- W2953182604 hasRelatedWork W2949720764 @default.
- W2953182604 hasRelatedWork W2950876001 @default.
- W2953182604 hasRelatedWork W2951826842 @default.
- W2953182604 hasRelatedWork W2952884182 @default.
- W2953182604 isParatext "false" @default.
- W2953182604 isRetracted "false" @default.
- W2953182604 magId "2953182604" @default.
- W2953182604 workType "article" @default.