The present paper describes the convenient stereospecific synthesis of the analogues of α- and β-D-glucose 1-phosphate. The β analogue, (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid, was synthesized by treatment of 2,6-anhydro-1-bromo-1-deoxy-3,4,5,7-tetra-O-acetyl-D-glycero-D-gluco-heptitol with triethyl phosphite, followed by deethylation of the obtained diethyl (1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methanephosphonate and deacetylation with ion-exchange resin. The a analogue, (1-deoxy-α-D-glucopyranosyl)methanephosphonic acid, was synthesized by starting from 2,3,4,6-tetra-O-benzyl-D-glucose through the following sequence: Wittig reaction with methylenetriphenylphosphorane, mercuriocyclization, bromodemercuriation, Arbuzov reaction, and removal of the protecting groups.

Stereospecific synthesis of the phosphono analogues of α- and β-D-glucose 1-phosphate / F. Nicotra, F. Ronchetti, G. Russo. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 47:23(1982), pp. 4459-4462.

Stereospecific synthesis of the phosphono analogues of α- and β-D-glucose 1-phosphate

F. Ronchetti
Secondo
;
G. Russo
Ultimo
1982

Abstract

The present paper describes the convenient stereospecific synthesis of the analogues of α- and β-D-glucose 1-phosphate. The β analogue, (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid, was synthesized by treatment of 2,6-anhydro-1-bromo-1-deoxy-3,4,5,7-tetra-O-acetyl-D-glycero-D-gluco-heptitol with triethyl phosphite, followed by deethylation of the obtained diethyl (1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methanephosphonate and deacetylation with ion-exchange resin. The a analogue, (1-deoxy-α-D-glucopyranosyl)methanephosphonic acid, was synthesized by starting from 2,3,4,6-tetra-O-benzyl-D-glucose through the following sequence: Wittig reaction with methylenetriphenylphosphorane, mercuriocyclization, bromodemercuriation, Arbuzov reaction, and removal of the protecting groups.
Settore BIO/10 - Biochimica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/182760
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 46
  • ???jsp.display-item.citation.isi??? ND
social impact