Stereoselective preparation of O-alkoxy d-tetrose, d-pentose, 2-deoxy-d-glycero tetrose and 2,3-dideoxy-d-erythro pentose derivatives by an iterative elongation of 2,3-O-isopropylidene-d-glyceraldehyde

Abstract All d -pentoses are synthesized by one-carbon chain elongation commencing with the addition of the lithium salt of ethyl ethylthiomethyl sulfoxide to 2- O -( t -butyldimethylsilyl)-3,4- O -isopropylidene- d -erythrose and d -threose, 16 and 17 . The addition of the above-mentioned nucleophile to 2-deoxy-3,4- O -isopropylidene- d -glycero tetrose, 19 , gave rise to 2,3-dideoxy- d -glycero pentose. The starting aldehydes, 16 , 17 and 19 , are easily available from 2,3- O -isopropylidene- d -glyceraldehyde, 1 , and ethyl ethylthiomethyl sulfoxide.