𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of methyl O-(3-deoxy-3-fluoro-β-d-galactopyranosyl)-(1→6)-β-d-galactopyranoside and methyl O-(3-deoxy-3-fluoro-β-d-galactopyranosyl)-(1→6)-O-β-d-galactopyranosyl-(1→6)-β-d-galactopyranoside

✍ Scribed by Pavol Kováč; Herman J.C. Yeh; Cornelis P.J. Glaudemans

Publisher
Elsevier Science
Year
1985
Tongue
English
Weight
828 KB
Volume
140
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

✦ Synopsis

Condensation of 2,4,6-tri-O-acetyl-3-deoxy-3-fluoro-cr-D-galactop~anosyl bromide (3) with methyl 2,3,4-tri-O-acetyl-/9-D-galactopyranoside (4) gave a fully acetylated (1+6)-/3-D-galactobiose fluorinated at the 3'-position which was deacetylated to give the title disaccharide. The corresponding trisaccharide was obtained by reaction of 4 with 2,3,4-tri-O-acetyl-6-O-chloroacetyl-a-o-galactopyranosyl bromide (5), dechloroacetylation of the formed methyl O-(2,3,4-tri-Oacetyl-6-0-chloroacetyl-~D-galactopyranosyl)-(1~6)-2,3,4-tri-O-acetyl-&D-galactopyranoside to give methyl 0-(2,3,4-tri-O-acetyl-~-D-galactopyranosyl)-(l~6)-2,3,4-tri-O-acetyl-pD-galactopyranoside (14), condensation with 3, and deacetylation. Dechloroacetylation of methyl O-(2,3,4-tri-O-acetyld-O-chloroacetyl-~-ogalactopyranosyl) -(1+6) -0 -(2,3,4 -tri -0 -acetyl -P-D -galactopyranosyl) -(1+6) -2,3,4-tri-0-acetyl-/3-D-galactopyranoside,

obtained by condensation of disaccharide 14 with bromide 5, was accompanied by extensive acetyl migration giving a mixture of products. These were deacetylated to give, crystalline for the first time, the methyl P_glycoside of (1-6)~/3-D-galactotriose in high yield. The structures of the target compounds were confirmed by 500-MHz, 2D, 'H-and conventional 13C-and lgF-n.m.r. spectroscopy.

📜 SIMILAR VOLUMES

Synthesis of methyl O-(3-deoxy-3-fluoro-
Synthesis of methyl O-(3-deoxy-3-fluoro-β-d-galactopyranosyl)-(1→6)-O-β-d-galactopyranosyl-(1→6)-3-deoxy-3-fluoro -β-d-galactopyranoside and related n.m.r. studies
✍ Pavol Kováč; Cornelis P.J. Glaudemans; Wie Guo; Tuck C. Wong 📂 Article 📅 1985 🏛 Elsevier Science 🌐 English ⚖ 966 KB

Sequential tritylation, benzoylation, and detritylation of methyl 3-deoxy-3fluoro-AD-galactop~~oside gave crystalline methyl 2,4-di-O-benzoyl-3-deoxy-3-~uoro-ED-gala~opyr~oside (9), which was used as the initial nucleophile in the synthesis of the target otigosaccha~de (16). Treatment of 9 with 2,3,

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

Efficient and stereoselective synthesis
Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-β-d-galactopyranosyl)-α-d-galactopyranoside and methyl 3,6-anhydro-4-O-β-d-galactopyranosyl-α-d-galactopyranoside
✍ Abdul Rashid; William Mackie 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 652 KB

Methyl 3-O-(3,6-anhydro-beta-D-galactopyranosyl)-alpha-D-galactopyranoside (3) and methyl 3,6-anhydro-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside (4) have been synthesised stereoselectively using three coupling procedures. Acceptable yields were achieved using acetylated derivatives as don

Synthetic mucin fragments: methyl 3-O-(2
Synthetic mucin fragments: methyl 3-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-β-d-galactopyranoside and methyl 3-O-(2-acetamido-2-deoxy-3-O-β-d-galactopyranosyl-β-d-glucopyranosyl)-β-d-galactopyranoside
✍ Katsunori Kohata; Saeed A. Abbas; Khushi L. Matta 📂 Article 📅 1984 🏛 Elsevier Science 🌐 English ⚖ 608 KB

Methyl 2,4,6-tri-O-benzyl-P-D-galactopyranoside (5) was obtained crystalline by way of its 3-O-ally] derivative, which was in turn obtained by ring-opening of a presumed 3,4-0-stannylene derivative of methyl p-D-galactopyranoside, followed by benzylation. Condensation of 5 with 2-methyl-(2-acetamido

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