Synthesis of Terminal Oligosaccharides from Type Specific Lipooligosaccharide of Mycobacterium Tuberculosis |
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Authors: | Mukund K Gurjar Sanjoy K Das Prathama S Mainkar |
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Institution: | Indian Institute of Chemical Technology , Hyderabad, 500 007, India |
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Abstract: | Abstract The coupling reaction between 1,3-di-O-acetyl-4-O-benzyl-2-O-methyl-α-L-rhamnopyranose (9) and methyl 4-O-benzyl-2-O-methyl-α-L-rhamno-pyranoside (4) was carried out in the presence of boron trifluoride-etherate followed by deacetylation to give the disaccharide (11) containing a free 3′ position. The second glycosylation reaction with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide in the presence of mercuric salts followed by removal of benzyl and acetyl groups provided the trisaccharide 2. The boron trifluoride catalysed condensation of 1,3,4-tri-O-acetyl-2-O-methyl-L-fucopyranose (14) and methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside (15) gave the disaccharide (16) from which the protecting groups were removed to form the disaccharide (3). |
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