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- W2037846645 abstract "The protected glycopeptide N-(benzyloxycarbonyl)-l-alanyl-[O-(2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→3)-O- (2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-(1→3)]-l-threonyl-l-alanine 2,2,2-trichloroethyl ester (21) was made by coupling the respective disaccharide and tripeptide blocks. The disaccharide block was generated by coupling tetra-O-benzoyl-α-d-galactopyranosyl bromide to allyl 2,4,6-tri-O-benzyl-α-d-galactopyranoside and converting the product into O-(2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-α-d-galactopyranosyl chloride (6) via the 1-propenyl glycoside and the free (1-OH) sugar. Alternatively, the 1-propenyl intermediate was obtained directly by using 1-propenyl 2,4,6-tri-O-benzyl-α-d-galactopyranoside (10) as the acceptor in the initial coupling reaction. An efficient 3-step synthesis of 10 was accomplished by the dibutyltin oxide-assisted, selective crotylation of allyl α-d-galactopyranoside at O-3, followed by benzylation and treatment of the product with potassium tert-butoxide. The N-benzyloxycarbonyl (Z) and N-tert-butoxycarbonyl (Boc) 2,2,2-trichloroethyl esters of Thr-Ala and Ala-Thr-Ala were formed by sequential coupling. The silver triflate-promoted glycosylation of the Z-protected dipeptide and tripeptide by 2,3,4,6-tetra-O-benzyl-α-d-galactopyranosyl chloride, and of the tripeptide by 6, proceeded with excellent α-stereoselectivity. From the disaccharide tripeptide 21, the carboxyl-deprotected and fully deprotected derivatives were prepared." @default.
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- W2037846645 date "1988-03-01" @default.
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- W2037846645 title "Synthesis of a close analog of the repeating unit of the antifreeze glycoproteins of polar fish" @default.
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- W2037846645 doi "https://doi.org/10.1016/0008-6215(88)85096-1" @default.
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