136522-38-8

Upstream product

• 91604-41-0 (R,R)-1,4-dibenzylthreitol 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 
• 17137-55-2 (2S,3S)-2,3-di(methanesulfonyloxy)-1,4-dibenzyloxybutane 
• 167937-19-1 (2R,3R)-1,4-dibenzyloxy-2,3-dimethanesulfonyloxybutane 

Relevant academic research and scientific papers

Synthesis, structure and reactivity of an Evans-type bis(imide) derived from a C2-symmetric bis(oxazolidinone). A reluctant chiral auxiliary

This paper describes the enantiospecific synthesis of the C2-symmetric bis(oxazolidinone) 9 from (-)-1,4-di-O-benzyl-L-threitol (3). Compound 9 was intended for use as a bifunctional chiral auxiliary in asymmetric alkylation and aldol reactions. However, in the presence of strong non-nucleophilic bases the bis(imide) derivative 10 (the structure of which has been studied in detail by means of NMR spectroscopy, X-ray crystallography and computational methods) did not react with external electrophiles. This lack of reactivity has been interpreted on the basis of a conformational analysis of 10.

Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers

(2R,3R)-2,3-Diaminobutane-1,4-diol 6 and its dibenzyl ether 7 were efficiently synthesized starting from L-tartaric acid 1a. The crucial step, debenzylation of intermediate dibenzyloxydiazide 4, was accomplished in good yield by boron trichloride-dimethyl sulfide complex. The enantiomeric series was similarly obtained starting from D-tartaric acid.