Syntheses of Branched Non‐1‐ynitols by Chemoselective Addition of (Trimethylsilyl)‐propargylmagnesium Bromide at the Anomeric Center of Side Chain Halogeno Functionalized Carbohydrates

Autor:	Paul Kipke, Sanjeev Kumar V. Vernekar, Hartmut Redlich
Rok vydání:	2008
Předmět:	chemistry.chemical_compound Anomer chemistry Trimethylsilyl Silylation Bromide Reagent Organic Chemistry Grignard reaction Side chain Organic chemistry Biochemistry Isomerization
Zdroj:	Journal of Carbohydrate Chemistry. 27:10-31
ISSN:	1532-2327 0732-8303
DOI:	10.1080/07328300801991278
Popis:	A convenient method for the syntheses of non‐1‐ynitols 8a–8d, by chemoselective addition of (trimethylsilyl)‐propargylmagnesium bromide at the anomeric center of a 1‐unprotected sugar, in the presence of 3‐C′‐halide and 3‐C′‐silyl functions in the side chain is described. In addition, an efficient method for the synthesis of 3‐C′‐hydroxymethyl sugar 3 via the addition of C1 silyl Grignard reagents to ulose 1 and subsequent oxidation by the Fleming‐Tamao method in excellent yields is reported. Also, a suitable acid‐catalyzed isomerization of the 1,2‐O‐isopropylidene group to the 2,3‐O‐isopropylidene group (5a–5f), to get access to the anomeric center, in good to excellent yields has been depicted.
Databáze:	OpenAIRE
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