408524-74-3

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 119593-27-0 (4S,5S)-5-<(phenylsulfonyl)amino>-4-allyl-2,2-dimethyl-1,3-dioxane 

Downstream Products

• 408524-78-7 (4S,5S)-5-(N-benzyloxymethyl-N-phenylsulfonyl)amino-4-(1'-methylene-2'-oxoethyl)-2,2-dimethyl-1,3-dioxane 
• 408524-80-1 (4S,5S)-5-(N-benzyloxymethyl-N-phenylsulfonyl)amino-4-[(1'S)-1'-methyl-2'-oxoethyl]-2,2-dimethyl-1,3-dioxane 
• 1026561-39-6 (4aS,6R,7S,7aS)-6-Methoxycarbonylmethyl-2,2,7-trimethyl-tetrahydro-[1,3]dioxino[5,4-b]pyrrole-5-carboxylic acid benzyl ester 
• 408524-85-6 (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-phenylcarbamoylpyrrolidine isopropylidene ketal 
• 408524-84-5 (2S,3S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal 
• 408524-82-3 (3S,4S,5S)-2,4-dihydroxy-5-hydroxymethyl-3-methyl-1-(phenylsulfonyl)pyrrolidine isopropylidene ketal 
• 408524-76-5 (4S,5S)-5-(N-benzyloxymethyl-N-phenylsulfonyl)amino-4-(2'-oxoethyl)-2,2-dimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Hydroxylated pyrrolidines. Enantiospecific synthesis of all-cis 2,3,4,5-substituted pyrrolidine derivatives from serine

We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven by a preference for hydrogenation from the rear side of the molecule. The all-cis configuration of these fully substituted pyrrolidines has been established by X-ray analysis of compound 6. Removal of the benzenesulfonyl group from the highly substituted and functionalized intermediate 15 is successfully accomplished by sodium naphthalenide reduction.