Boger, Dale L.; Panek, James S. published the artcile< Preparation of (R)-(+)- and (S)-(-)-4-iodo-1,2-epoxybutane [(R)- and (S)-(2-iodoethyl)oxirane], useful chiral synthons>, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate, the main research area is iodoepoxybutane stereoselective preparation; epoxybutane iodo stereoselective preparation; malic acid reduction; butanetriol base catalyzed ring closure; iodoethyloxirane stereoselective preparation; oxirane iodoethyl stereoselective preparation.
S-Epoxybutane I (R = iodo) was prepared by LiAlH4 reduction of S-R1CH2CH(OR2)R1 (II; R1 = MeO2C, R2 = 2-tetrahydropyranyl) followed by mesylation and hydrolysis to give S-II (R1 = CH2OSO2Me, R2 = H) which was treated with K2CO3 to give S-I (R = OSO2Me) which was then iodinated by NaI. Reduction of S-II (R1 = CO2Me, R2 = MeOCMe2) followed by acetylation in the presence of 4-dimethylaminopyridine gave S-II (R1 = AcOCH2) (III). III was hydrolyzed and then mesylated to give S-II (R2 = OSO2Me) which was treated with K2CO3 and MeOSO2Cl to give R-I (R = CH2OSO2Me) (IV). Treating IV with NaI at 25° gave R-I (R = iodo).
Journal of Organic Chemistry published new progress about 617-55-0. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics