[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamic acid 1,1-dimethylethyl ester, CAS No. 144163-85-9

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144163-85-9

Catalog No. EBD47438

CAS 144163-85-9

Name [(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamic acid 1,1-dimethylethyl ester

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Basic Information

Synonyms: Carbamicacid,[(1s,2s,4s)-4-amino-3-Hydroxy-5-phenyl-1-phenylmethyl]pentyl-1,1-dimethylethylester (2S,3S,5S)-2-Amino-3-Hydroxy-5(T)-Butyloxycarbonylamino-1,6-Diphenyl-HexaneSuccinicAcid (2S,3S,5S)-2-Amino-3-Hydroxy-5-(Tert-Butyloxycarbonylamino)-1,6-DiphenylHexaneSuccinicAcid (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino-1,6-diphenyl-hexanesuccinicacid (2S,3S,5S)-5-(Tert-butyloxycarbonyl)amino-2-amino-3-hydroxy-1,6-diphenylhexane tert-butyl[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate BDH [(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-carbamicacid1,1-dimethylethylester tert-butyl(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-ylcarbamate [(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamicacid1,1-dimethylethylester (2S,3S,5S)-5-tert-butyloxycarbonylamino-2-amino-3-hydroxy-1,6-diphenylhexane (2S,3S,5S)-5-(Tert-butyloxycarbonyl)amino-2-amino-3-hydroxy-1,6-diphenylhexane(BDH) (2S,3S,5S)-5-(Tert-butoxybonyl)ami

Molecular Formula: C23H32N2O3

Molecular Weight: 384.51

MDL Number: MFCD09833420

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

This compound, known as [(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic acid tert-butyl ester, is a chiral, protected amino alcohol derivative. It features a tert-butyloxycarbonyl (Boc) protecting group on the amine, a benzyl group, and a phenyl substituent, all attached to a stereochemically defined pentane backbone with hydroxyl and amino functionalities. The specific (1S,3S,4S) stereochemistry is crucial for its intended applications. Its primary and well-documented application is as a key chiral building block or intermediate in the synthesis of complex pharmaceutical agents. Most notably, it serves as a critical precursor in the synthesis of HIV protease inhibitors, such as Atazanavir and related compounds. The defined stereocenters and functional groups in this molecule are essential for constructing the core structure of these drugs, which work by inhibiting the viral protease enzyme, preventing the maturation of infectious HIV particles. As a Boc-protected amino alcohol, it is designed for use in peptide coupling and solid-phase peptide synthesis (SPPS) strategies, facilitating the controlled assembly of peptide-like drug molecules. Its role is strictly as a high-value synthetic intermediate in medicinal chemistry research and pharmaceutical development, rather than a commodity chemical or a reagent for general synthesis.

Physical Properties

Boiling Point: 569.182 °C at 760 mmHg

Flash Point: 298.03 °C

Density: 1.111 g/cm3

Analytical Data

Appearance: Powder