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A protected trisaccharide imidate, 2,3-di-O-acetyl-4,6-O-benzylidene-β-d-glucopyranosyl-(1→3)-2-O-chloroacetyl-3-O-benzyl-4-isobutyryl-α-l-rhamnopyranosyl-(1→4)-2-O-isobutyryl-α-l-rhamnopyranosyl trichloroacetimidate (1), has been synthesized by a block synthesis approach. Compound 1 can serve as a key intermediate in the total synthesis of resin glycoside merremoside H 2 .
The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-α-l-rhamnopyranosides was selectively acylated in 56–78% yields by reaction with 1.1equiv of acyl chloride in the presence of 1.5equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D.
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