129467-48-7

Basic information

• Product Name: benzyl [(5S,8S,9R,10R,11S,14S)-8,11-dibenzyl-9,10-dihydroxy-15-methyl-3,6,13-trioxo-1-phenyl-5-(propan-2-yl)-2-oxa-4,7,12-triazahexadecan-14-yl]carbamate (non-preferred name)
• Synonyms: L-Iditol, 1,2,5,6-tetradeoxy-2,5-bis[[(2S)-3-methyl-1-oxo-2-[[(phenylmethoxy)carbonyl]amino]butyl]amino]-1,6-diphenyl-
• CAS NO: 129467-48-7
• Molecular Formula: C₄₄H₅₄N₄O₈
• Molecular Weight: 766.9216
• Mol File: 129467-48-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 995.9°C at 760 mmHg
• Flash Point: 556.1°C
• Density: 1.205g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: benzyl [(5S,8S,9R,10R,11S,14S)-8,11-dibenzyl-9,10-dihydroxy-15-methyl-3,6,13-trioxo-1-phenyl-5-(propan-2-yl)-2-oxa-4,7,12-triazahexadecan-14-yl]carbamate (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl [(5S,8S,9R,10R,11S,14S)-8,11-dibenzyl-9,10-dihydroxy-15-methyl-3,6,13-trioxo-1-phenyl-5-(propan-2-yl)-2-oxa-4,7,12-triazahexadecan-14-yl]carbamate (non-preferred name)(129467-48-7)
• EPA Substance Registry System: benzyl [(5S,8S,9R,10R,11S,14S)-8,11-dibenzyl-9,10-dihydroxy-15-methyl-3,6,13-trioxo-1-phenyl-5-(propan-2-yl)-2-oxa-4,7,12-triazahexadecan-14-yl]carbamate (non-preferred name)(129467-48-7)

Safety Data

• Hazardous Substances Data: 129467-48-7(Hazardous Substances Data)

Upstream product

• 10512-93-3 Z-Val-ONp 
• 134878-07-2 (2S,3R,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane 
• 134805-49-5 (2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 137649-86-6 (2S,3R,4R,5S)-2,5-Diamino-1,6-diphenyl-3,4-hexanediol Dihydrochloride 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 63700-05-0 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 
• 136740-98-2 2S,5S-Diazido-1,6-diphenyl-3,4-O-isopropylidenehexane-3R,4R-diol 
• 138328-92-4 (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol 
• 136740-96-0 (2R,3R,4R,5R)-3,4-O-isopropylidene-1,6-diphenyl-2,3,4,5-hexanetetraol 
• 162920-22-1 O²,O⁵-diacetyl-1,6-dichloro-O³,O⁴-isopropylidene-1,6-dideoxy-D-mannitol 
• 69-65-8 mannitol 
• 148743-43-5 N-benzyloxycarbonyl-L-valyl-L-phenylalaninol 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 134805-50-8 (2S,3R,4R,5S)-2,5-bis(N-valinylamino)-3,4-dihydroxy-1,6-diphenylhexane 

Relevant articles and documents

Vanadium(II)- and Niobium(III)-Induced, Diastereoselective Pinacol Coupling of Peptide Aldehydes to Give a C2-Symmetrical HIV Protease Inhibitor

Peptide aldehydes 15a-c are prepared without epimerization from enantiomerically pure (S)-α-amino acids (Scheme 3).Reductive pinacol homocoupling of 15a-c, induced by vanadium complex 11 or niobium complex 16 in refluxing THF, yields C2-symmetr

Symmetry-Based Inhibitors of HIV Protease. Structure-Activity Studies of Acylated 2,4-Diamino-1,5-diphenyl-3-hydroxypentane and 2,5-Diamino-1,6-diphenylhexane-3,4-diol

The structure-activity relationships in two series of novel, symmetry-based inhibitors of HIV protease, the enzyme responsible for maturation of the human immunodeficiency virus, are described.Beginning with lead compounds 3-6, the effect of adding polar, heterocyclic end groups to one or both ends of the symmetric or pseudosymmetric inhibitors was probed.Aqueous solubility was enhanced >1000-fold while maintaining potent inhibition of purified HIV-1 protease and anti-HIV activity in vitro.Pharmacokinetic studies in rats indicated a substantial difference in the absorption properties of mono-ol-based and diol-based inhibitors.The oral bioavailability of inhibitor 19 in rats was 19percent; however, the Cmax obtained failed to exceed the anti-HIV EC50 in vitro.Substantial plasma levels of potent inhibitors of the diol class were not obtained after oral administration in rats; however, the optimal combination of aqueous solubility and in vitro antiviral activity of several inhibitors support their potential use in intravenous therapy.

Stereocontrolled synthesis of HIV-1 protease inhibitors with C2-axis of symmetry

An efficient and stereocontrolled synthesis of various C2-symmetric HIV-1 protease inhibitors is described, starting from commercially available and inexpensive D-mannitol.