Benzyl 2-azido-2-deoxy-β-d-galactopyranoside was converted into benzyl 2-azido-4,6-O-benzyl-2-deoxy-β-d-galactopyranoside via benzylidenation, p-methoxybenzylation, acid hydrolysis, benzylation, and selective oxidation. Condensation of 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose with benzyl 2-azido-4,6-di-O-benzyl-2-deoxy- β-d-galactopyranoside in the presence of trimethylsilyl triflate gave crystalline benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-d-gal actopyranosyl)-β-d-galactopyranoside (76%), which was converted into benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-β-d-galactopyr anosyl)-β-d-galactopyranoside and condensed with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranosyl bromide in the presence of silver silicate on alumina and molecular sieve 4 Å to give 61% of benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-d-galactopyranosyl)- (1→4)-O-(2,6-di-O-benzyl-β-d-galactopyranosyl)-(1→3)-2- azido-4,6-di-O-benzyl-2-deoxy-β-d-galactopyranoside. Reduction with sodium borohydride followed by N-acetylation, O-deacetylation, and catalytic hydrogenolysis then gave O-(2-acetamido-2-deoxy-β-d-galactopyranosyl)-(1→4)-O-β-d- galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-galactopyranose, the desialylated human Cad-antigenic determinant.

CHEMICAL SYNTHESIS OF THE DESIALYLATED HUMAN CAD-ANTIGENIC DETERMINANT

CATELANI, GIORGIO;
1986

Abstract

Benzyl 2-azido-2-deoxy-β-d-galactopyranoside was converted into benzyl 2-azido-4,6-O-benzyl-2-deoxy-β-d-galactopyranoside via benzylidenation, p-methoxybenzylation, acid hydrolysis, benzylation, and selective oxidation. Condensation of 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose with benzyl 2-azido-4,6-di-O-benzyl-2-deoxy- β-d-galactopyranoside in the presence of trimethylsilyl triflate gave crystalline benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-d-gal actopyranosyl)-β-d-galactopyranoside (76%), which was converted into benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-β-d-galactopyr anosyl)-β-d-galactopyranoside and condensed with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranosyl bromide in the presence of silver silicate on alumina and molecular sieve 4 Å to give 61% of benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-d-galactopyranosyl)- (1→4)-O-(2,6-di-O-benzyl-β-d-galactopyranosyl)-(1→3)-2- azido-4,6-di-O-benzyl-2-deoxy-β-d-galactopyranoside. Reduction with sodium borohydride followed by N-acetylation, O-deacetylation, and catalytic hydrogenolysis then gave O-(2-acetamido-2-deoxy-β-d-galactopyranosyl)-(1→4)-O-β-d- galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-galactopyranose, the desialylated human Cad-antigenic determinant.
Catelani, Giorgio; Marra, A; Paquet, F; Sinay, P.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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: http://hdl.handle.net/11568/15241
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 8
  • ???jsp.display-item.citation.isi??? 8
social impact