99666-07-6

Upstream product

• 143-33-9 sodium cyanide 
• 78513-07-2 (-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol 
• 99665-85-7 (2S,3R)-1-(benzyloxy)-4-(tert-butylthio)-2,3-butanediol 
• 78513-07-2 ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol 

Downstream Products

• 103927-51-1 D-O-Benzyl-2-deoxyxylic acid 
• 141503-28-8 (1E,3S)-4-benzyloxy-1-cyano-1-buten-3-ol 
• 103927-52-2 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone 
• 72605-53-9 γ-benzyloxymethyl-α,β-butenolide 

Relevant academic research and scientific papers

Selective Transformation of 2,3-Epoxy Alcohols and Related Derivatives. Strategies for Nucleophilic Attack at Carbon-1

In connection with the continuing recent interest in the stereoselective synthesis of epoxy alcohols, a systematic investigation of the bimolecular nucleophilic ring-opening reactions of acyclic 2,3-epoxy alcohols was undertaken.Strategies for nucleophilic attack at C-1 of a 2,3-epoxy alcohol, each of which depends upon the regioselective ring-opening of a 1,2-epoxy 3-ol, were explored.Under Payne rearrangement conditions, t-BuSNa was found to react with 2,3-epoxy alcohols to afford 1-tert-butylthio 2,3-diols.These diols can be readily converted to 1,2-epoxy 3-ols via S-alkylation followed by treatment with base.Alternatively, 1,2-epoxy 3-ols can be prepared from 2,3-epoxy alcohols by sulfonylation and acidic hydrolysis followed by ring-closure of the diol sulfonate intermediate.Dialkylamines were also found to react selectively with 2,3-epoxy alcohols under Payne rearrangement conditions to afford 1-amino 2,3-diols.