Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy |
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Authors: | Babu Boga Sobhana Balasubramanian Kalpattu Kuppuswamy |
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Institution: | Department of Chemistry, Indian Institute of Technology, Madras, Chennai 600 036, India. |
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Abstract: | Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as 6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose. |
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Keywords: | Glycal Fructofuranose Deuterated fructofuranose Ozonolysis Isotopic labelling Ketohexofuranose Aldohexopyranose |
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