TY - JOUR
T1 - Synthesis of a Deoxynojirimycin Analogue from Castanospermine
AU - Bremner, J.B.
AU - Skelton, Brian
AU - Smith, R.J.
AU - Tarrant, G.J.
AU - White, Allan
PY - 1996
Y1 - 1996
N2 - 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
AB - 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
U2 - 10.1016/0040-4039(96)01959-4
DO - 10.1016/0040-4039(96)01959-4
M3 - Article
VL - 37
SP - 8573
EP - 8576
JO - Tetrahedron Letters
JF - Tetrahedron Letters
ER -