✦ LIBER ✦

Synthesis of benzyl O-(2-O-methyl-β-d-galactopyranosyl)-(1→3)-2-acetamido-2-deoxy-β-d-glucopyranoside [benzyl 2′-O-methyllacto-N-bioside I], and its higher saccharide containing an O-(2-O-methyl-β-d-galactopyranosyl)-(1→3)-2-acetamido-2-deoxy-β-d-glucopyranosyl group as a potential substrate for (1→4)-α-l-fucosyltransferase

✍ Scribed by Arun K. Sarkar; Rakesh K. Jain; Khushi L. Matta

Publisher: Elsevier Science
Year: 1990
Tongue: English
Weight: 1002 KB
Volume: 203
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(90)80043-3

No coin nor oath required. For personal study only.

✦ Synopsis

Treatment of benzyl O-/?-n-galactopyranosyl-( 1+3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-j3-D-glucopyranoside with tert-butylchlorodiphenylsiiane afforded the 6'-0-tert-butyldiphenylsilyl ether, which was converted into the 3',4'-0-isopropylidene derivative. Methylation and subsequent removal of protecting groups afforded henzyl O-(2-O-methyl-/I-D-galactopyranosyl)-( 1+3)-2-acetamido-2-deoxy-j&oglucopyranoside (7). The trisaccharide methyl 0-(2-0-methyl-/?-n-galactopyranosyl)-( 1+3)-0-(2-acetamido-2-deoxy-@glucopyranosyl)-( l-+3)-B-D-galactopyranoside (17) and the tetrasaccharide O-(2-O-methyl$-D-galactopyranosyl)-( 1-+3)-0-(2-acetamido-2-deoxy-jk1-glucopyranosyl)-( l-3)-O-@galactopyranosyl-( 1+4)-o-glucopyranose (32), both containing the 2'-0-methyllacto-N-biose I unit at the nonreducing end, were synthesized, and the structures of 7,17, and 32 were confirmed by "C-n.m.r. spectrosco-PY.

📜 SIMILAR VOLUMES

Synthetic mucin fragments. Benzyl O-(2-a

Synthetic mucin fragments. Benzyl O-(2-acetamido-2-deoxy-α-d-glucopyranosyl)-(1→3)-O-β-d-galactopyranosyl-(1→3)-O- [(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6)]-2-acetamido-2-deoxy-α-d-galactopyranoside and benzyl O-(2-acetamido-2-deoxy- β-d-glucopyranosyl)-(1→3)-O-β-d-galactopyranosyl-(1→3)-O-[β-d-galactopyranosyl-(1→6)]-2-acetamido-2-deoxy-α-d- galactopyranoside

✍ Rexford L. Thomas; Saeed A. Abbas; Khushi L. Matta 📂 Article 📅 1988 🏛 Elsevier Science 🌐 English ⚖ 713 KB

Treatment of benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with 4-methoxybenzaldehyde dimethyl acetal in N,N-dimethylformamide in the presence of 4-toluenesulfonic acid afforded the 4,6-O-(4-methoxybenzylidene) acetal, which was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosy

Synthesis of methyl O-(2-O-methyl-β-d-ga

Synthesis of methyl O-(2-O-methyl-β-d-galactopyranosyl)-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)- β-d-galactopyranoside and 4-nitrophenyl O-β-d-galactopyranosyl-(1 → 4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-β-d-galactopyranoside

✍ Shaheer H. Khan; Rakesh K. Jain; Khushi L. Matta 📂 Article 📅 1990 🏛 Elsevier Science 🌐 English ⚖ 704 KB

Recent years have seen a remarkable surge of interest in the study of U-Lfucosyltransferases. Of these L-fucosyltransferases, the enzyme (143)~a+fucosyltransferase has attracted a great deal of clinical interest as a potential tumor marker. This enzyme catalyzes the transfer of an L-fucosyl group f

Synthesis of benzyl O-(3-O-methyl-β-d-ga

Synthesis of benzyl O-(3-O-methyl-β-d-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-α-d-galactopyranoside and benzyl O-(β-d-galactopyranosyl)-(1 → 3)-2-acetamido-2-deoxy-6-O-methyl-α-d-galactopyranoside as specific acceptors for sialyltransferases

✍ Rakesh K. Jain; Conrad F. Piskorz; E.V. Chandrasekaran; Khushi L. Matta 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 304 KB

Synthesis of benzyl 2-acetamido-2-deoxy-

Synthesis of benzyl 2-acetamido-2-deoxy-3-O-β-d-fucopyranosyl-α-d-galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-2-deoxy-3-O-β-d-fucopyranosyl-α-d-galactopyranoside

✍ Conrad F. Piskorz; Saeed A. Abbas; Khushi L. Matta 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 428 KB

Condensation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-galactopyranoside with 2,3,4-tri-o-acetyl-a-D-fucopyranosyl bromide in 1: 1 nitromethane-benzene, in the presence of powdered mercuric cyanide, afforded benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-0-(2,3,4-tri-O-acetyl-P-D-fucopyran

Synthesis of p-nitrophenyl 2-acetamido-2

Synthesis of p-nitrophenyl 2-acetamido-2-deoxy-4-O-β-d-galactopyranosyl- β-d-glucopyranoside, and p-nitrophenyl 6-O-(2-acetamido-2-deoxy-3-O- and -4-O-β-d-galactopyranosyl- β-d-glucopyranosyl)-α-d-mannopyranoside

✍ Surjit S. Rana; Joseph J. Barlow; Khushi L. Matta 📂 Article 📅 1983 🏛 Elsevier Science 🌐 English ⚖ 885 KB

A synthesis of 8-methoxycarbonyloct-1-yl

A synthesis of 8-methoxycarbonyloct-1-yl O-α-d-galactopyranosyl-(1→3)-O-β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

✍ Per J. Garegg; Stefan Oscarson 📂 Article 📅 1985 🏛 Elsevier Science 🌐 English ⚖ 480 KB

Halide-assisted glycosyIation, using a non-p~icipating Z-substituent (benzyl) in the glycosyl halide, was used to obtain the ~-D-gaiactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the /3-D-galactosyl linkage in a facile synthesis of the t