Synthesis of O-(2-Deoxy-2-stearoylamino-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine, a Lipophilic Disaccharide Analogue of MDP
1992 ◽
Vol 57
(3)
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pp. 579-589
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Partial N-deacetylation of compound II with barium hydroxide afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O,-benzyl-2-deoxy-α-D-glucopyranoside (III) in high yield. Compound III was N-acylated with stearic acid in the presence of DCC and the obtained product was converted into benzyl 2-acetamido-6-O-benzyl-3-O-carboxymethyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-α-D-glucopyranoside (VII). Coupling of compound VII with L-α-aminobutanoyl-D-isoglutamine benzyl ester followed by hydrogenolysis of the product VIII afforded compound IX.
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1988 ◽
Vol 46
◽
pp. 418-419
1990 ◽
Vol 48
(4)
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pp. 876-877
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2002 ◽
Vol 28
(2)
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pp. 103-111
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2020 ◽
Vol 21
(1)
◽
pp. 6-9
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2009 ◽
Vol 21
(5)
◽
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