158807-47-7

Basic information

• Product Name: (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL
• Synonyms: (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL ;(R)-(3-Hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester;Boc-R-3-amino-3-phenylpropan-1-ol;tert-butyl (2R)-2-aMino-4-hydroxy-2-phenylbutanoate;(R)-Boc-3-amino-3-phenylpropan-1-ol;(R)-tert-Butyl (3-hydroxy-1-phenylpropyl)carbamate
• CAS NO: 158807-47-7
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.32144
• Mol File: 158807-47-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 404.6 °C at 760 mmHg
• Flash Point: 198.5 °C
• Appearance: /
• Density: 1.083 g/cm³
• Storage Temp.: 2-8°C
• PKA: 11.77±0.46(Predicted)
• CAS DataBase Reference: (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL(158807-47-7)
• EPA Substance Registry System: (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL(158807-47-7)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 158807-47-7(Hazardous Substances Data)

Usage

General Description

(R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is a chemical compound with the molecular formula C15H23NO3. It is an amino alcohol derivative with a BOC (tert-butyloxycarbonyl) protecting group attached to the nitrogen atom. (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is commonly used in organic synthesis as a chiral building block for the preparation of pharmaceuticals and other biologically active compounds. It has a chiral center at the 3-position and a phenyl group attached to the propyl chain, making it suitable for use in asymmetric synthesis and medicinal chemistry. (R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL is a versatile intermediate that can be used in the production of a wide range of compounds with diverse applications.

Upstream product

• 305806-21-7 tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate 
• 1234571-68-6 S,S'-bis(2,6-dimethylphenyl) 2-(R)-((tert-butoxycarbonylamino)(phenyl)methyl)propanebisthioate 
• 161024-80-2 (R)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid 
• 1315566-29-0 C₁₅H₂₁NO₃ 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 103-54-8 cinnamyl acetate 
• 58377-44-9 N-(tert-butoxycarbonyl)-O-methylhydroxylamine 
• 85217-69-2 cinnamyl methyl carbonate 
• 124517-47-1 cinnamyl tert-butyl carbonate 
• 158851-29-7 (+)-tert-butyl [(1R)-1-phenylprop-2-en-1-yl]imidocarbonate 
• 936499-92-2 (R)-3-amino-3-phenylpropan-1-ol hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-52-7 benzaldehyde 
• 1624-53-9 2-(benzylideneamino)phenol 

Downstream Products

• 908290-50-6 (R)-4-phenyl-(1,3)-oxazinan-2-one 
• 908290-70-0 (R)-3-propanoyl-4-phenyl-(1,3)-oxazinan-2-one 

Relevant articles and documents

Chiral N,N′-Dioxide/Tm(OTf)3 Complex-Catalyzed Asymmetric Bisvinylogous Mannich Reaction of Silyl Ketene Acetal with Aldimines

An enantioselective bisvinylogous Mannich reaction of silyl ketene acetal with aldimines has been realized by using a chiral N,N′-dioxide/Tm(OTf)3 complex as catalyst, providing an effective method to synthesize chiral ζ-amino-α,β,γ,δ-unsaturated carbonyl compounds. (Figure presented.).

Direct Asymmetric Vinylogous and Bisvinylogous Mannich-Type Reaction Catalyzed by a Copper(I) Complex

A direct catalytic asymmetric vinylogous Mannich-type reaction has been disclosed in good yield, excellent regio-, diastereo- and enantioselectivity. The key to control the regioselectivity is the combination of a bulky N-acylpyrazole and a bulky bisphosphine ligand. The catalytic system was extended to a bisvinylogous Mannich-type reaction by changing the ligand. The synthetic utility of the vinylogous products was demonstrated by several transformations.

Which is the actual catalyst: Chiral phosphoric acid or chiral calcium phosphate?

(Figure Presented) Both catalysts work: A highly enantioselective direct Mannich-type reaction of NBoc-protected aldimines with 1,3-dicarbonyl compounds has been developed with the use of a chiral phosphoric acid in the presence or absence of Ca . The absolute stereoselectivity of the phosphoric acid catalysis was found to be opposite to that of the calcium phosphate catalysis (see scheme; Boc = tert-butoxycarbonyl).