74044-76-1

Upstream product

• 53754-41-9 1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 74044-75-0 (2R,3R,4R,5R)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 38195-12-9 (R)-1-formylethyl p-toluenesulfonate 
• 171524-74-6 1,6-dideoxy-D-mannitol 2,5-di-p-toluenesulfonate 

Relevant academic research and scientific papers

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

A convergent synthesis of optically active aspyrone

Aspyrone (1) was elaborated in an optically pure form by the key reaction involving a nucleophilic addition of δ-lactone enolate to 2-tosyloxyaldehyde and a subsequent in situ formation of epoxide.