156038-50-5

Upstream product

• 78513-07-2 (-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol 
• 1027578-88-6 ((4R,5R)-5-Benzyloxymethyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-ylmethoxy)-tert-butyl-dimethyl-silane 
• 151359-20-5 (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate 

Downstream Products

• 127505-66-2 (2R,3S)-1-(Benzyloxy)-2,3-octanediol 
• 85118-86-1 (2R,3S)-1-(Benzyloxy)-2,3-butanediol 

Relevant academic research and scientific papers

C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Application and Synthesis of Naturally Occuring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly.In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols.Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occuring (S,S)-2,3-octanediol and (R,R)-muricatacin.The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides.The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols.This methodology has been applied to the asymmetric synthesis of naturally occuring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction.Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate.Upon desilylation, this compound undergoes a Payne-type rearrangement.Nucleophilic epoxide-opening then provides an erythro-2,3-diol.The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel.Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures.Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, -N3, -OAc, -CN, halides as well as carbon nucleophiles and hydride.