308140-75-2

Upstream product

• 131380-35-3 (2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al 
• 1027573-79-0 2-{(S)-[(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranyl]-trimethylsilanyloxy-methyl}-thiazole 
• 308140-72-9 (1S,2R,3S)-4-tert-Butyldiphenylsilyloxy-2,3-epoxy-1-(thiazol-2-yl)butanol 
• 308140-87-6 (2S,3S)-4-tert-Butyldiphenylsilyloxy-2,3-epoxy-1-(thiazol-2-yl)butan-1-one 
• 77-76-9 2,2-dimethoxy-propane 
• 308140-73-0 (1S,2S,3R)-3-Azido-4-tert-butyldiphenylsilyloxy-2-hydroxy-1-(thiazol-2-yl)butanol 

Downstream Products

• 308140-76-3 (4S,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 308140-77-4 (4R,5S)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 308140-78-5 {(4S,5S)-5-[(R)-1-Amino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 308365-83-5 (2S,3S,4R)-4-Azido-2,3-dioxyisopropylidene-5-tert-butyldiphenylsilyloxypentanol 
• 308140-79-6 (2S,3S,4R)-4-(tert-Butyloxycarbonylamino)-2,3-dioxyisopropylidene-5-tert-butyldiphenylsilyloxypentanol 
• 308140-80-9 (2S,3S,4R)-4-(tert-Butyloxycarbonylamino)-1-O-carbamoyl-2,3-dioxyisopropylidene-5-tert-butyldiphenylsilyloxypentanol 

Relevant academic research and scientific papers

De novo asymmetric synthesis of protected 5-O-carbamoylpolyoxamic acid

The synthesis of 5-O-carbamoylpolyoxamic acid from a non carbohydrate precursor was achieved in 12 steps and 7% yield starting from chiral α,β-epoxyaldehyde readily available from cis-2-butene-1,4-diol. The main steps concern the Sharpless asymmetric epoxidation of a suitable chosen allylic alcohol, the use of thiazolyl group for carbon homologation, the stereo- and regioselective opening of the epoxide and the transformation of the primary alcohol to the acid functionality of the final product.