Sobhana Babu, Boga ; Balasubramanian, Kalpattu Kuppusamy (2005) Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy Carbohydrate Research, 340 (4). pp. 753-758. ISSN 0008-6215
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00086...
Related URL: http://dx.doi.org/10.1016/j.carres.2005.01.008
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Glycal; Fructofuranose; Deuterated Fructofuranose; Ozonolysis; Isotopic Labelling; Ketohexofuranose; Aldohexopyranose |
| ID Code: | 3731 |
| Deposited On: | 18 Oct 2010 09:54 |
| Last Modified: | 12 Jan 2011 07:11 |
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