596128-74-4

Upstream product

• 544455-38-1 ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate 
• 100-44-7 benzyl chloride 
• 544455-39-2 (2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester 

Downstream Products

• 596128-78-8 [2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenoxymethyl)-propyl]-carbamic acid tert-butyl ester 
• 596128-77-7 N-[2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-phenoxymethyl)-propyl]-acetamide 
• 825633-70-3 (2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-2-(4-methoxy-phenoxymethyl)-5-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 825633-71-4 (2R,3S,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-2-(4-methoxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 825633-63-4 [(1R,2S,3R)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester 
• 825633-61-2 (2S,3R)-2-Benzyloxy-3-tert-butoxycarbonylamino-4-(4-methoxy-phenoxy)-butyric acid ethyl ester 
• 851724-09-9 [(1R,2S)-2-Benzyloxy-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Hg(II) reagent-controlled stereoselective synthesis of 2,5-cis- and 2,5-trans-polyhydroxylated pyrrolidines

Stereoselectivity in the intramolecular amidomercuration reaction of 11, which could form 2,5-cis- and 2,5-trans-polyhydroxylated pyrrolidines, was found to be dependent on the nature of the Hg(II) salts used as well as on the stereochemistry and protection state of the hydroxyl group at the allylic carbon. Thus, the amidomercuration reaction of 11 with Hg(CF3CO 2)2 led to the predominant formation of the 2,5-cis-polyhydroxylated pyrrolidine 16, while use of Hg(CF3SO 3)2 generated the corresponding 2,5-trans isomer 17. Isomers 16 and 17 were further elaborated to stereoselectively synthesize 2,5-dideoxy 2,5-imino-D-altritol and 2,5-dideoxy 2,5-imino-D-galactitol (for 20 and 21), which are known to be potent D-galactosidase inhibitors.

A concise and general methodology for the complete asymmetric synthesis of the orthogonally protected 2-amino-1,3,4-butanetriols (ABTs)

A complete asymmetric synthesis of the orthogonally protected 2-amino-1,3,4-butanetriols I (ABTs: versatile four carbon chiral synthons) was accomplished via the regioselective asymmetric aminohydroxylation (AA) reaction and oxazoline chemistry in four to six steps from the starting olefin 1. The syn-vicinal amino alcohol functionality of I was installed by the regioselective AA reaction of the achiral olefin 1 in a single step, and the anti-vicinal amino alcohol functionality of I was derived from the syn-amino alcohol 2 by inverting the C2 hydroxy group stereochemistry through the formation and hydrolysis of the oxazoline 7. Thus, the present strategy represents the most efficient and general asymmetric synthesis of ABTs so far.