Journal
ORGANIC LETTERS
Volume 20, Issue 11, Pages 3413-3417Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01355
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Funding
- National Institutes of Health [R01-GM115779]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM115779] Funding Source: NIH RePORTER
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A concise synthesis of a branched trisaccharide, alpha-L-Dig-(1 -> 3)-[alpha-L-Eva-(1 -> 4)]-beta-n-Fuc, corresponding to saccharomicin B, has been developed via reagent-controlled a-selective glycosylations. Starting from the D-fucose acceptor, L-epivancosamine was selectively installed using 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropene-1-thione/oxalyl bromide mediated dehydrative glycosylation. Following deprotection, L-digitoxose was installed using the AgPF6/TTBP thioether-activation method to produce the trisaccharide as a single a-anomer. This highly functionalized trisaccharide can potentially serve as both a donor and an acceptor for the total synthesis of the antibiotic saccharomicin B.
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