TY - JOUR
T1 - Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives
AU - Gilbert, Ian H.
AU - Holmes, Andrew B.
AU - Pestchanker, Mauricio J.
AU - Young, Rodney C.
PY - 1992/10/9
Y1 - 1992/10/9
N2 - Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) With di isobytylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol (6). 2,4,5,6-Tetra-O-benzyl-1,3-O-methylene-DL-myo-inositol (16) reacted with allyltrimethylsilane in the presence of Lewis acids to give 2,4,5,6-tetra-0-benzyl-1-O-(3-butenyl)-DL-myo-inositol [(+/-)-17] or rearranged to give 4,5,6-tri-O-benzyl-1,2-0-methylene-DL-myo-inositol [+/-)-18].
AB - Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) With di isobytylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol (6). 2,4,5,6-Tetra-O-benzyl-1,3-O-methylene-DL-myo-inositol (16) reacted with allyltrimethylsilane in the presence of Lewis acids to give 2,4,5,6-tetra-0-benzyl-1-O-(3-butenyl)-DL-myo-inositol [(+/-)-17] or rearranged to give 4,5,6-tri-O-benzyl-1,2-0-methylene-DL-myo-inositol [+/-)-18].
U2 - 10.1016/0008-6215(92)85043-Y
DO - 10.1016/0008-6215(92)85043-Y
M3 - Article
SN - 0008-6215
VL - 234
SP - 117
EP - 130
JO - Carbohydrate Research
JF - Carbohydrate Research
ER -