Repozytorium

Reactivity and crystal structure of 1,2:3,4:5,6-tri-O-isopropylidene-D-gluconolactone.

Autorzy

Sławomir Jarosz

Zbigniew Ciunik

Rok wydania

1998

Czasopismo

Polish Journal of Chemistry

Numer woluminu

72

Strony

1182-1190

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

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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