The synthesis of deoxygalactostatin and 2,6-imino-heptitol derivatives via stannane mediated hydroxymethylation of 5-azido-1,4-lactones

Synlett

Volumn , Issue 5, 1998, Pages 554-556

  Shilvock, John P ^a   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002482313     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1698     Document Type: Article

References (34)

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25. Typical Experimental Procedure for Stannane Mediated Hydroxymethylation Butyllithium (2.5 M solution in hexanes, 1.22 ml, 3.05 mmol) was added to a stirred solution of tribulyl[(methoxymethoxy)-methyl]stannane 7 (1.27 g, 3.52 mmol) in THF (5 ml) at -78°C. After 5 min, a solution of the requisite 5-azido-aldono-1,4-lactone (2.35 mmol) in THF (5 ml) was added. The solution was stirred at -78°C for 30 min and the reaction mixture was quenched by the addition of saturated ammonium chloride solution (1 ml) and partitioned between water (75 ml) and ethyl acetate (3x50 ml). The combined organic phase was washed with brine (50 ml), dried (magnesium sulfate), filtered and concentrated in vacuo. The residue was subjected to flash chromatography on silica to afford the 6-azido-2-ketofuranose.
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30. 3,4 3.1, H-3).
31. 2O) 54.6, 56.0 (2d, C-2, C-6), 62.1 (t, C-1, C-7), 66.7, 70.1, 71.7 (3d, C-3, C-4, C-5).
32. 2O) 53.9, 57.2 (2d, C-6, C-2), 57.5, 62.6 (2t, C-1, C-7), 69.6, 71.6 (3d, C-3, C-4, C-5).
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34. 2O) 11.5 (q, C-7), 51.3, 53.0 (2d, C-6, C-2), 62.1 (t, C-1), 70.2, 70.6, 70.8 (3d, C-3, C-4, C-5).