Preparation, X-ray structure and reactivity of a stable glycosyl iodide.
Highly selective reaction of methyl tetra-O-pivaloyl-beta-D-glucopyranuronate 2 with iodotrimethylsilane or (Me3Si)2 and I2 affords, in excellent yield, the 'disarmed' glycosyl iodide 1 which has good stability at 20 degrees C and excellent stability at 0 degrees C; the X-ray crystal structure of 1 is described, along with a comparison of its utility as a glycosyl donor to that of the corresponding bromide.
Bickley
Jamie
J
The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool, UK L69 7ZD.
Cottrell
Jennifer A
JA
Ferguson
John R
JR
Field
Robert A
RA
Harding
John R
JR
Hughes
David L
DL
Kartha
K P Ravindanathan
KP
Law
Jayne L
JL
Scheinmann
Feodor
F
Stachulski
Andrew V
AV
D005947:Glucose / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D014961:X-Ray Diffraction
D007454:Iodides; D005947:Glucose