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Reactivity and crystal structure of 1,2:3,4:5,6-tri-O-isopropylidene-D-gluconolactone.
Autorzy
Rok wydania
1998
Czasopismo
Numer woluminu
72
Strony
1182-1190
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
1,2:3,4,5,6-Tri-O-isopropylidene-D-gluconate (1) undergoes the beta-elimination reaction in the presence of LDA to afford 3-deoxy-1,2:5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone (6). Attempts to prepare the phosphonate 4 by reaction of 1 with dimethyl methylphosphonate in the presence of LDA failed; only elimination product 6 was isolated from the reaction mixture. The sugar phosphonate 8 (protected form of 4) was prepared from methyl 2-O-benzyl-3,4:5,6-di-O-isopropylidene gluconate (7) by reaction with (-)CH2P(O)(OMe)2. The crystal structure of 1 is reported.
Słowa kluczowe
gluconolactone triacetonide, sugar phosphonates, beta-elimination
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