46122-47-8

Upstream product

• 108-24-7 acetic anhydride 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 2584-71-6 cis-hydroxy-D-proline 
• 51-35-4 4R-4-hydroxyproline 
• 229027-68-3 methyl (S)-4-(4,4'-dimethoxytrityloxy)-L-prolinate 
• 229027-61-6 methyl (R)-4-(4,4'-dimethoxytrityloxy)-L-prolinate 
• 229027-60-5 methyl (R)-N-allyloxycarbonyl-4-(4,4'-dimethoxytrityloxy)-L-prolinate 
• 229027-67-2 methyl (S)-N-allyloxycarbonyl-4-(4,4'-dimethoxytrityloxy)-L-prolinate 
• 229027-62-7 methyl (R)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate 
• 229027-69-4 methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate 
• 152722-89-9 (2R,4R)-4-Hydroxy-2-methylprolin 

Relevant academic research and scientific papers

Synthesis of DNA-(3')-PNA chimeras with conformationally restricted linkers based on 4-hydroxyproline

The synthesis and evaluation of DNA-(3')-PNA chimeras containing rigid linkers based on (R/S)-4-hydroxy-D/L-proline are described. It is shown that installment of the trans-L-linker using the tetrabutylammonium salt of (R)- 4-(4,4'-dimethoxytrityloxy)-N-(thymin-l-yl)acetyl-L-proline (2) leads to a DNA-(3')-PNA chimera which hybridizes efficiently with complementary RNA.

Alkylation in the 2-Position of (2S,4R)-4-Hydroxyproline with Retention of Configuration

O-Acetyl-4-hydroxyproline (1b) is condensed with pivalaldehyde to give a single stereoisomer of the 2-(tert-butyl)-4-oxo-3-oxa-1-azabicyclooct-7-yl acetate (3).This is converted to the enolates 4 or 5, reactions of which with alkyl halides, aldehydes, and acetone (-->6,9,10,11) are diastereoselective (lk-1,3-induction).Cleavage of the corresponding products furnishes the enantiomerically pure 2-deuterio-, 2-methyl-, 2-allyl-, and 2-benzyl-substituted 4-hydroxyprolines 2a-2d.