1372138-70-9

Basic information

• Product Name: (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol
• Synonyms: (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol
• CAS NO: 1372138-70-9
• Molecular Weight: 434.533
• Mol File: 1372138-70-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol(1372138-70-9)
• EPA Substance Registry System: (1S,2R,3R)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)-2,3-epoxyhexanol(1372138-70-9)

Safety Data

• Hazardous Substances Data: 1372138-70-9(Hazardous Substances Data)

Upstream product

• 14468-80-5 N-benzyloxycarbonylpyrrolidin-2-one 
• 69261-54-7 1-(benzyloxycarbonyl)pyrrolidin-2-ol 
• 1372138-69-6 (1R,E)-6-benzyloxycarbonylamino-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)hex-2-en-1-ol 
• 1372138-68-5 (E)-6-(benzyloxycarbonylamino)-1-((S)-N-tert-butoxycarbonylpyrrolidin-2-yl)hex-2-en-1-one 

Downstream Products

• 1372138-74-3 C₃₀H₄₀N₂O₆ 

Relevant articles and documents

Synthesis and biological activity of potent HIV-1 protease inhibitors based on Phe-Pro dihydroxyethylene isosteres

Peptidomimetic inhibitors of HIV-1 PR are still a key resource in the fight against AIDS. Here we describe the synthesis and biological activity of HIV-1 PR inhibitors based on four novel dihydroxyethylene isosteres of the Phe-Pro and Pro-Pro dipeptides. The isosteres, containing four stereogenic centers, were synthesized in high yield and excellent stereoselectivity via the cyclization of epoxy amines derived from α-amino acids. The inhibitors were assembled by coupling the isosteres with suitable flanking groups and were screened against recombinant HIV PR showing activities in the subnanomolar to micromolar range. Two Phe-Pro-based inhibitors active at the nanomolar level were further investigated: both inhibitors combine the ability to suppress HIV-1 replication in infected MT-2 cells with low cytotoxicity against the same cells, thereby displaying a high therapeutic index. These results demonstrate the potential of the new Phe-Pro dihydroxyethylene isostere as a core unit of powerful HIV-1 PR inhibitors.