Synthesis of a Deoxynojirimycin Analogue from Castanospermine

J.B. Bremner, Brian Skelton, R.J. Smith, G.J. Tarrant, Allan White

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7 Citations (Scopus)


Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 with methyl chloroformate followed by deprotection with tetrabutylammonium fluoride gave (1S,6S,7R,8R,8aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, 8,8a-hexahydro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with potassium t-butoxide, followed by the addition of NaOH and futher refluxing yielded the deoxynojirimycin analogue (1'S,2R,3R,4R,5S)-2-(1'-hydroxy-2'-propenyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd
Original languageEnglish
Pages (from-to)8573-8576
JournalTetrahedron Letters
Publication statusPublished - 1996


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