Synthesis of all possible regioisomers of scyllo-inositol phosphate.
scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis-diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo-IPn.
Chung
S K
SK
Department of Chemistry, Pohang University of Science and Technology, South Korea. skchung@postech.ac.kr
Kwon
Y U
YU
Chang
Y T
YT
Sohn
K H
KH
Shin
J H
JH
Park
K H
KH
Hong
B J
BJ
Chung
I H
IH
D007294:Inositol / Q000138:chemical synthesis / Q000737:chemistry; D007295:Inositol Phosphates / Q000737:chemistry*; D013237:Stereoisomerism
D007295:Inositol Phosphates; D007294:Inositol