229030-08-4

Upstream product

• 100-39-0 benzyl bromide 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 78987-06-1 C₄H₄O₃^(2-)*2Li⁽¹⁺⁾ 

Downstream Products

• 1365541-27-0 (3R,4S)-3-allyl-3-benzyl-4-hydroxydihydrofuran-2(3H)-one 
• 1365541-56-5 methyl ((S)-1-(2-(2-((3S,4S)-3-benzyl-4-hydroxy-1-((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)-2-oxopyrrolidin-3-yl)ethyl)-2-(4-bromobenzyl)hydrazinyl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate 
• 1365541-36-1 (3R,4S)-3-allyl-3-benzyl-4-((tert-butyldimethylsilyl)oxy)-1-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-2,3-dihydro-1H-inden-1-yl)pyrrolidin-2-one 
• 229159-10-8 (2S,3S)-2-Benzyl-3,4-dihydroxy-butyramide 

Relevant academic research and scientific papers

Synthesis, X-ray analysis, and biological evaluation of a new class of stereopure lactam-based HIV-1 protease inhibitors

In an effort to identify a new class of druglike HIV-1 protease inhibitors, four different stereopure β-hydroxy γ-lactam-containing inhibitors have been synthesized, biologically evaluated, and cocrystallized. The impact of the tether length of the central spacer (two or three carbons) was also investigated. A compound with a shorter tether and (3R,4S) absolute configuration exhibited high activity with a Ki of 2.1 nM and an EC50 of 0.64 μM. Further optimization by decoration of the P1′ side chain furnished an even more potent HIV-1 protease inhibitor (Ki = 0.8 nM, EC50 = 0.04 μM). According to X-ray analysis, the new class of inhibitors did not fully succeed in forming two symmetric hydrogen bonds to the catalytic aspartates. The crystal structures of the complexes further explain the difference in potency between the shorter inhibitors (two-carbon spacer) and the longer inhibitors (three-carbon spacer).

Synthesis of N-BOC-3-amino-1,2-epoxy-4-phenylbutane from (3S)-hydroxy-γ-butyrolactone by means of the Hofmann rearrangement

The stereocontrolled synthesis of the title alkylaminoepoxide was achieved starting from (3S)-hydroxy-γ-butyrolactone by efficient utilization of the Hofmann rearrangement followed by intramolecular oxazolidinone ring formation as a key step.

Stereoselective Alkylation and Aldol Reactions of (S)-(-)-β-Hydroxy-γ-butyrolactone Dianion

The dianion of 3 reacts with alkyl halides to give exclusively trans-2-alkyl-3-hydroxy lactones and with aldehydes to give 2,3-trans-disubstituted lactones which exhibit erythro selectivity in the newly formed aldol moiety.