Lewis acid-catalysed rearrangements of Myo-inositol orthoformate derivatives

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 -