Strategy in Oligosaccharide Synthesis:  An Application to a Concise Total Synthesis of the KH-1(adenocarcinoma) Antigen

A concise and potentially practical synthesis of the title compound has been achieved. The route features a high degree of convergence and economy of synthetic operations. A key step is the concurrent introductory addition of three α-l-fucosyl residues at required hydroxyl acceptor sites (see 37 → 3...

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Published inJournal of the American Chemical Society Vol. 120; no. 7; pp. 1600 - 1614
Main Authors Deshpande, Prashant P, Kim, Hyunjin M, Zatorski, Andrzej, Park, Tae-Kyo, Ragupathi, Govindaswami, Livingston, Philip O, Live, David, Danishefsky, Samuel J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.02.1998
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
LEY
FUCOLIPIDS
GLYCALS
CARBOHYDRATE ANTIGENS
TISSUES
SIALYL-LEWIS-X
ABERRANT GLYCOSYLATION
HUMAN ADENOCARCINOMA
CANCER
III3FUCV3FUCVI2FUCNLC6
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Summary:A concise and potentially practical synthesis of the title compound has been achieved. The route features a high degree of convergence and economy of synthetic operations. A key step is the concurrent introductory addition of three α-l-fucosyl residues at required hydroxyl acceptor sites (see 37 → 39). Conjugation to carrier protein was achieved, and a route to include truncated structures for investigations for antibody specificity was accomplished.
Bibliography:istex:F14A0A4E9497365859232EAD867F89B99421B08B
ark:/67375/TPS-D1BHPVPB-P
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9725864