Diastereoselective synthesis of D- and L-myo-inositol 3,4,5,6-tetrakisphosphates from D-glucose via dihydroxylation of (+)-conduritol B derivatives.
Syntheses of D- and L-myo-inositol 3,4,5,6-tetrakisphosphates were achieved via diastereoselective 1,2-addition of vinylcopper reagent with the chiral aldehyde prepared from 1,2,5,6-diisopropylidene-D-glucose, ring-closing metathesis of 1,7-diene with Grubbs catalyst followed by catalytic OsO(4) dihydroxylation of (+)-conduritol B derivatives.
Saito
Shintaro
S
Research and Education Center for Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0101, Japan.
Shimazawa
Rumiko
R
Shirai
Ryuichi
R
D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000378:metabolism; D053138:Cyclohexenes; D005947:Glucose / Q000138:chemical synthesis* / Q000378:metabolism; D006900:Hydroxylation; D007295:Inositol Phosphates / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000378:metabolism; D013237:Stereoisomerism
D003511:Cyclohexanols; D053138:Cyclohexenes; C490694:D-myo-inositol 3,4,5,6-tetrakisphosphate; D007295:Inositol Phosphates; C090988:conduritol B; D005947:Glucose