Improved synthesis of enantiopure pseudo-C2-symmetric 1,4-bis-epoxide building blocks from arabitol

An improved large-scale synthesis of 1,2:4,5-dianhydro-3-benzylarabitol and 1,2:4,5-dianhydroarabitol from arabitol is described.

Figure optionsDownload as PowerPoint slide

(2S,4S)-1,5-Di-O-(2,4,6-triisopropyl-benzenesulfonyl)-arabitolC35H56O9S2Ee = 100%[α]D24=-1.4 (c 2.2, CHCl3)Source of chirality: starting materialAbsolute configuration: (2S,4S)

(2S,4S)-1,2:4,5-Dianhydro-3-(benzyl)-arabitolC12H14O3Ee = 100%[α]D24=-27.8 (c 1.6, CHCl3)Source of chirality: starting materialAbsolute configuration: (2S,4S)