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

• Autorzy: Jarosz, S. , Ciunik, Z.
• Języki publikacji: EN

Abstrakty

EN

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

EN

gluconolactone triacetonide; sugar phosphonates; beta-elimination

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 1998
• Tom: Vol. 72, nr 7
• Strony: 1182-1190
• Opis fizyczny: Bibliogr. 15 poz., tab.

Twórcy

autor

Jarosz, S.

autor

Ciunik, Z.

• Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44 01-224 Warszawa Poland,