129491-65-2

Basic information

• Product Name: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-L-altritol
• Synonyms: L-Altritol, 1,2,5,6-tetradeoxy-2,5-bis(((1,1-dimethylethoxy)carbonyl)amino)-1,6-diphenyl-
• CAS NO: 129491-65-2
• Molecular Formula: C₂₈H₄₀N₂O₆
• Molecular Weight: 500.627
• Mol File: 129491-65-2.mol
• Article Data: 4

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-L-altritol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-L-altritol(129491-65-2)
• EPA Substance Registry System: 2,5-bis[(tert-butoxycarbonyl)amino]-1,2,5,6-tetradeoxy-1,6-diphenyl-L-altritol(129491-65-2)

Safety Data

• Hazardous Substances Data: 129491-65-2(Hazardous Substances Data)

Usage

Molecular weight

493.59 g/mol

Structure

A tetradeoxy sugar derivative with two protected amino groups ((tert-butoxycarbonyl)amino) and two phenyl groups, based on the L-altritol core.

Use as a chiral auxiliary

TBAT is often utilized as a chiral auxiliary in asymmetric synthesis, meaning it can help induce chirality in a reaction to create chiral products with high enantioselectivity.

Reagent for selective cleavage

TBAT is also used as a reagent for the highly selective cleavage of esters and lactones, which can be useful in the synthesis of complex organic molecules.

Unique structure and reactivity

TBAT's unique structure and reactivity make it a valuable tool in the design and synthesis of complex organic molecules.

Potential applications

TBAT has potential applications in the fields of medicinal chemistry and drug development, due to its ability to create chiral compounds and its selective reactivity.

Upstream product

• 72155-45-4 Boc-L-phenylalaninal 
• 247575-73-1 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 247575-93-5 (2S,3S,4R,5S)-2,5-Bis-dibenzylamino-1,6-diphenyl-hexane-3,4-diol 
• 247575-91-3 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2R,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-hydroxy-4-phenyl-butyl ester 
• 247575-87-7 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-oxo-4-phenyl-butyl ester 

Downstream Products

• 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 
• 143838-09-9 (4S,5R,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one) 

Relevant articles and documents

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.

Stereocontrolled Synthesis of C2-Symmetric and Pseudo-C2-Symmetric Diamino Alcohols and Diols for Use in HIV Protease Inhibitors

The stereocontrolled syntheses of dibenzyldiamino alcohol 1 and dibenzyldiamino diols 2-4, core units of potent C2-symmetric and pseudo-C2-symmetric inhibitors of HIV protease, are described, starting from phenylalanine.Stereoselecti