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- W2059352912 abstract "Optically pure D-(+)-N-methylfucosamine (8) has been synthesized from a TBDMS-protected methyl L-serinate benzophenone Schiff base (O'Donnell's Schiffbase, 1) in seven steps in 13% overall yield. Efficient construction of the requisite amino triol acetate 3a with the proper stereochemical configuration is accomplished in two steps with a chelation-controlled reduction-alkylation reaction using |Bu 2 AlH.A-iBu 3 /E-LiCH=CHCH 3 , followed by oxidation with OsO 4 . Conversion of the Schiff base to the N-benzhydryl protecting group and methylation (Eschweiler-Clark) is accomplished in one pot with NaCNBH 3 in the presence of H 2 C=0. Deprotection and oxydation of the primary alcohol, followed by deacetylation with KCN, provides the desired product 8" @default.
- W2059352912 created "2016-06-24" @default.
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- W2059352912 date "2010-08-18" @default.
- W2059352912 modified "2023-09-25" @default.
- W2059352912 title "ChemInform Abstract: An Enantioselective Synthesis of N-Methylfucosamine via Tandem C-C/C-O Bond Formation." @default.
- W2059352912 cites W2949872891 @default.
- W2059352912 doi "https://doi.org/10.1002/chin.199506230" @default.
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