111265-96-4

Upstream product

• 405215-53-4 N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 
• 5211-24-5 (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 111193-60-3 (S)-3,4-Dihydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 191851-84-0 (2S,3R,4S)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-2-pyrrolidinylcarboxylic acid 
• 111193-62-5 (2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester 

Downstream Products

• 160711-63-7 (2R,3R,4S)-1-benzyloxycarbonyl-2-hydroxymethylpyrrolidine-3,4-diol 
• 111193-68-1 (3aR,4S,6aS)-2,2-Dimethyl-4-methylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 111193-67-0 (3aR,4S,6aS)-4-((S)-3-Amino-3-carboxy-propylsulfanylmethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 1632124-95-8 (2R,3R,4S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-pyrrolidine-3,4-diol 
• 1632125-08-6 C₃₀H₄₆N₄O₄ 
• 1055041-51-4 C₃₀H₃₆N₆O₁₄P₂ 
• 208658-24-6 (2R,3R,4S)-2-[(phosphooxy)methyl]pyrrolidine-3,4-diol 
• 105990-41-8 (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol 
• 317357-80-5 methyl 4-[(3R,4S)-isopropylidenedioxy-1-[4-[N-(2-methylphenyl)ureido]-3-methoxyphenylacetyl]-(2R)-pyrrolidinyl]methoxybenzoate 
• 317357-81-6 methyl 4-[(3R,4S)-dihydroxy-1-[4-[N-(2-methylphenyl)ureido]-3-methoxyphenylacetyl]-(2R)-pyrrolidinyl]methoxybenzoate 
• 317357-79-2 methyl 4-[(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate 
• 317357-78-1 methyl 4-[1-benzyloxycarbonyl-(3R,4S)-isopropylidenedioxy-(2R)-pyrrolidinyl]methoxybenzoate 
• 1053262-99-9 (3aR,4R,6aS)-2,2-Dimethyl-4-phosphonooxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 148252-71-5 (2R,3R,4S)-1-(benzyloxycarbonyl)-2-<(phosphooxy)methyl>pyrrolidine-3,4-diol 

Relevant academic research and scientific papers

Synthesis and cancer growth inhibitory activities of 2-fatty-alkylated pyrrolidine-3,4-diol derivatives

A series of new amphiphilic pyrrolidines containing dodecyl and oleyl apolar side chains were prepared and evaluated for their ability to inhibit the growth of pancreatic ductal adenocarcinoma cells in vitro. The new compounds are shown to exhibit anticancer activity at concentrations in the μM range. ARKAT-USA, Inc.

4-(Pyrrolidinyl)methoxybenzoic acid derivatives as a potent, orally active VLA-4 antagonist

A novel series of benzoic acid derivatives as VLA-4 antagonists were synthesized. Optimization, focusing on activity and lipophilicity needed for cell permeability, resulted in the identification of 15b and 15e with good activity (IC50=1.6 nM each) and moderate lipophilicity (Log D=2.0, 1.8). Furthermore, 15e demonstrated efficacy in murine asthma model by an oral dose of 30 mg/kg.

VLA-4 inhibitor compounds

Compounds that selectively inhibit the binding of ligands to alpha4beta1 integrin (VLA-4) and methods for their preparation are disclosed. In one embodiment, compounds of the invention are represented by Formula I: As selective inhibitors of VLA-4 mediated cell adhesion, compounds of the present invention are useful in the treatment of conditions associated with such adhesion, including, but not limited to, such conditions as inflammatory and autoimmune responses, diabetes, asthma, psoriasis, inflammatory bowel disease, transplantation rejection, and tumor metastasis. Also disclosed are pharmaceutical compositions, methods of inhibiting VLA-4 mediated cell adhesion and methods of treating conditions associated with LA-4 mediated cell adhesion, which involve compounds of Formula I.

Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives

(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters.The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave hi