1043894-59-2

Upstream product

• 1043894-58-1 (4R,5R)-4,5-dicyclohexyl-2-(azidomethyl)-1,3,2-dioxaborolane 
• 75-09-2 dichloromethane 
• 2146-67-0 (dichloromethyl)lithium 

Downstream Products

• 1043894-60-5 (4R,5R)-4,5-dicyclohexyl-2-(4-methoxybenzyloxy)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Synthesis of a (β-acetamido-α-acetoxyethyl)boronic ester via azido boronic esters

(Azidomethyl)boronic esters of 1,2-dicyclohexyl-1,2-ethanediol ( DICHED ) and pinanediol have been prepared from the corresponding (bromomethyl)boronic esters. Conversion to (2-azido-1-chloro- or bromoethyl)boronic esters by reaction with a (dihalomethyl)lithium followed. Attempted displacement of halide from DICHED (2-azido-1-haloethyl)boronates with alkoxides failed. Reaction of either pinanediol or DICHED (2-azido-1-chloromethyl)boronate with sodium acetate in acetic acid yielded the 1-acetoxy derivative as a ～1:1 mixture of diastereomers, indicating probable involvement of an α-boryl carbocation intermediate. Hydrogenation of the pinanediol azido boronic ester over platinum in a solution of hydrogen chloride in dioxane was accompanied by deacetylation to form the impure (2-amino-1-hydroxyethyl)boronic ester hydrochloride. Attempted purification of this material resulted in deboronation to ethanolamine. Acetylation yielded pinanediol (2-acetamido-1-acetoxyethyl)boronate.