129491-64-1

Basic information

• Product Name: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-D-mannitol
• CAS NO: 129491-64-1
• Molecular Formula: C₂₈H₄₀N₂O₆
• Molecular Weight: 500.627
• Mol File: 129491-64-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 680.3°C at 760 mmHg
• Flash Point: 365.2°C
• Density: 1.15g/cm³
• Vapor Pressure: 1.94E-19mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-D-mannitol(129491-64-1)
• EPA Substance Registry System: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-D-mannitol(129491-64-1)

Safety Data

• Hazardous Substances Data: 129491-64-1(Hazardous Substances Data)

Upstream product

• 168846-62-6 (2S,5S)-2,5-bis-<(1,1-dimethylethoxy)carbonylamino>-1,6-diphenylhex-3-ene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 247575-97-9 (2S,3S,4S,5S)-2,5-Bis-dibenzylamino-1,6-diphenyl-hexane-3,4-diol 
• 1004316-38-4 (3-benzenesulfonyl-1-benzyl-4-tert-butoxycarbonylamino-2-hydroxy-5-phenyl-pentyl)-benzyl-carbamic acid tert-butyl ester 
• 99306-88-4 (2S)-2-Benzylideneamino-3-phenylpropan-1-ol 
• 168846-63-7 (2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene 
• 158380-73-5 N-(tert-butoxycarbonyl)-N-benzyl-L-phenylalaninol 
• 158380-76-8 N-benzyl-N-(tert-butoxycarbonyl)-L-phenylalaninal 
• 141403-49-8 (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-phenyl-O-(4-methylphenylsulfonyl)propan-1-ol 
• 109687-70-9 tert-butyl (S)-(1-phenyl-3-(phenylthio)propan-2-yl)carbamate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 108385-55-3 2(S)-<(tert-butoxycarbonyl)amino>-3-phenyl-1-(phenylsulphonyl)propane 
• 42807-45-4 N-benzyl-L-phenylalaninol 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 137820-85-0 (2S,3S,4S,5S)-2,5-bis[(tert-butoxycarbonyl)amino]-1,6-dicyclohexylhexane-3,4-diol 
• 143838-08-8 (4S,5S,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one) 
• 134878-07-2 (2S,3R,4S,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane 
• 134878-06-1 (2S,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol 

Relevant articles and documents

A short approach to the synthesis of the ritonavir and lopinavir core and its C-3 epimer via cross metathesis

A short synthesis of hydroxyethylene dipeptide isostere, a core unit of the HIV-protease inhibitors ritonavir and lopinavir, its C-3 epimer and C2 symmetric diamino diol is described. The crucial aspects of the synthesis are self-cross metathesis and exploitation of C2-symmetric of the metathesis product 8 to obtain the required skeleton.

Facile and highly stereoselective synthesis of the C2-symmetrical diamino diol core-unit of HIV-1 protease inhibitors and of their symmetrical and unsymmetrical analogs from lithiated 2-(dibenzylamino)alkyl carbamates: Oxidative dimerization

The lithio derivatives of (S)-and (R)-2-(N,N-dibenzylamino)alkyl carbamates 3 and ent-3, generated by substrate-directed deprotonation from the precursors 2 and ent-2, add with high diastereoselectivity to (S)-2-(N,N- dibenzylamino)alkanals. The (S)-aminoaldehyde 5a, derived from (S)- phenylalanine, is produced in situ from the lithium compound 3a by the controlled addition of dioxygen to the reaction mixture affording the protected anti,syn,anti-α,δ-diamino-β,γ-diol 6aa which is the core unit of anti-HIV 1 protease agents. Several symmetric and unsymmetric structure analogs, differing in the substitution pattern and the configurations, have been synthesized. A further approach to the title compound is given by the acylation of lithium derivatives 3/4, followed by a hydride reduction. The reaction of the lithium derivatives 3a/4a with CuCl leads to an eliminative oxidative coupling with formation of (3 E/Z, 2S,5S)-2,5-dibenzylamino-1,6- diphenylhex-3-enes (E)- and (Z)-26.

Synthesis of a novel C2-symmetrical (2S,5S)-2,5-bis-[(1,1 -dimethylethoxy) carbonylamino]-1,6-diphenylhex-3-ene: Applications in the synthesis of potential HIV protease inhibitors

The synthesis of a novel and versatile (2S,5S)-2,5-bis-[(1,1′-dimethylethoxy)carbonylamino]-1,6-diphenylhex-3-ene (2) based on Julia's olefination strategy coupled with its application in stereoselective preparations of HIV protease inhibitors has been discussed.