5-N,4-O-Carbonyl-7,8,9-tri-O-chloroacetyl-Protected Sialyl Donor for the Stereoselective Synthesis of α-(2→9)-Tetrasialic Acid
The Journal of Organic Chemistry2010Vol. 75(15), pp. 4921–4928
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Chang‐Ching Lin, Nai-Pin Lin, L. Sk Sahabuddin, Vijaya Raghava Reddy, Li‐De Huang, Kuo Chu Hwang, Chun‐Cheng Lin
Abstract
An efficient stereoselective synthesis of alpha-(2-->9)-tetrasialic acid was achieved using tri-O-chloroacetyl-derivatized sialyl donor and a triol sialyl acceptor. Both the acceptor and the donor were also protected with a cyclic 5-N-4-O-carbonyl protecting group. The donor is highly reactive and enabled alpha-selective sialylation with various primary, secondary, and tertiary acceptors under in situ activation conditions (NIS/TfOH, -78 degrees C, acetonitrile/dichloromethane). The trans-fused oxazolidinone ring and O-chloroacetyl protecting groups were easily removed under mild reaction conditions to provide the fully deprotected alpha(2-->9)-tetrasialic acid.
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