73004-31-6

Usage

Chemical class

Pyrrolidines

Stereochemistry

(2S,4R)

Functional groups

Ester, carboxylic acid

Substituents

a. Phenylmethyl group
b. Phenylmethoxy group

Potential applications

a. Pharmaceuticals
b. Agrochemicals
c. Material science

Structural features

a. Chiral molecule
b. Unique arrangement of functional groups and substituents

Research status

Further research required to fully understand properties and potential uses.

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 51-35-4 4R-4-hydroxyproline 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 850741-43-4 (1S,5S)-6-(4,4-diphenylbut-3-en-1-yl)-2-oxa-6-azabicyclo[3.2.1]octan-3-one 
• 850741-39-8 methyl (2S,4R)-1-(4,4-diphenylbut-3-en-1-yl)-4-hydroxypyrrolidine-2-acetate 
• 850741-24-1 methyl (2S,4R)-4-benzyloxy-1-benzyloxycarbonylpyrrolidine-2-acetate 
• 850741-08-1 [(2S,4R)-1-(4,4-Diphenyl-but-3-enyl)-4-hydroxy-pyrrolidin-2-yl]-acetic acid 
• 850741-45-6 (1S,5S)-6-{2-[tris(4-methoxyphenyl)methoxy]-1-ethyl}-2-oxa-6-azabicyclo[3.2.1]octan-3-one 
• 850741-41-2 methyl (2S,4R)-4-hydroxy-1-{2-[tris(4-methoxyphenyl)-methoxy]-1-ethyl}pyrrolidine-2-acetate 
• 850741-15-0 ((2S,4R)-4-Hydroxy-1-{2-[tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidin-2-yl)-acetic acid 
• 871810-83-2 (2S,4R)-benzyl 4-(benzyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Chemoselective synthesis of N-protected alkoxyprolines under specific solvation conditions

N-Protected hydroxyprolines (Hyp) were transformed chemoselectively into alkoxyproline derivatives by direct O-alkylation. The starting Hyp was transformed into the corresponding dianion in a mixture of dimethyl sulfoxide and tetrahydrofuran (1:16 v/v) as solvent. Under these conditions, the carboxy-anion showed reduced nucleophilicity because it was specifically solvated, and the more reactive oxy-anion was selectively alkylated. N-Protected trans-4-alkoxy-, cis-4-alkoxy- and trans-3-alkoxyprolines were thus obtained in a single step in very high overall yields and with complete stability of the stereogenic center configuration. Copyright

Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds

The substitution of the 4-position of hydroxyproline by a phenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the α-functionalization of a wide range of linear/ branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and α-amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.

Synthesis and Pharmacological Activity of Angiotensin Converting Enzyme Inhibitors: N-(Mercaptoacyl)-4-substituted-(S)-prolines

The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described.These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition.The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril.The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.