Carbon-branched carbohydrate chirons: practical access to both enantiomers of 2-C
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- 作者：Kathrine V. Booth ; Filipa P. da Cruz ; David J. Hotchkiss ; Sarah F. Jenkinson ; Nigel A. Jones ; Alex ; er C. Weymouth-Wilson ; Robert Clarkson ; Thomas Heinz ; George W.J. Fleet
- 刊名：Tetrahedron: Asymmetry
- 出版年：2008
- 出版时间：20 October 2008
- 年：2008
- 卷：19
- 期：20
- 页码：2417-2424
- 全文大小：273 K
文摘
Readily crystallized 2-C-methyl-d-ribono-1,4-lactone is formed in a one-pot procedure from d-glucose without any protecting groups by treatment with dimethylamine to give an Amadori ketose and then with aqueous calcium hydroxide in yields of approximately 25 % ; 2-C-methyl-l-ribono-1,4-lactone is similarly produced from l-glucose. 3,4-O-Isopropylidene-2-C-methyl-d-arabinono-1,5-lactone and 2-C-methyl-d-arabinono-1,4-lactone were prepared in a combined 60 % yield by the Kiliani reaction of sodium cyanide with a protected 1-deoxy-d-ribulose derived from d-erythronolactone; the enantiomeric arabinonolactones are similarly available from l-erythronolactone.