63328-00-7

Basic information

• Product Name: N,O-Ditosyl D-Phenylalaninol
• Synonyms: N,O-Ditosyl D-Phenylalaninol;(S)-4-Methyl-N-[1-[[[(4-Methylphenyl)sulfonyl]oxy]Methyl]-2-phenylethyl]benzenesulfonaMide
• CAS NO: 63328-00-7
• Molecular Formula: C₂₃H₂₅NO₅S₂
• Molecular Weight: 460
• Product Categories: Amino Acids & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 63328-00-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,O-Ditosyl D-Phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-Ditosyl D-Phenylalaninol(63328-00-7)
• EPA Substance Registry System: N,O-Ditosyl D-Phenylalaninol(63328-00-7)

Safety Data

• Hazardous Substances Data: 63328-00-7(Hazardous Substances Data)

Usage

Description

N,O-Ditosyl D-Phenylalaninol is a chemical compound that serves as a protected form of D-Phenylalaninol. It is commonly used in the synthesis of various compounds and as an intermediate in the production of pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
N,O-Ditosyl D-Phenylalaninol is used as a protected form of D-Phenylalaninol for the synthesis of possible metabolites and enantiomers of Prolintane (P756100). It is also used as a possible intermediate in the synthesis of L-Amphetamine (A634240).
Used in Chemical Synthesis:
N,O-Ditosyl D-Phenylalaninol is used as a protecting group in the synthesis of various compounds, allowing for selective reactions to occur without affecting the D-Phenylalaninol moiety. This protection allows for the controlled synthesis of complex molecules and the development of new pharmaceuticals and chemical compounds.

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 63328-06-3 (4R)-4-amino-5-phenylpentanoic acid 
• 139925-41-0 R-N-Tosyl-1-phenyl-2-aminopentan 
• 132161-97-8 (S)-N-(1-Cyano-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide 
• 875438-87-2 (3S)-[N-(3-methyl-2-enyl)-N-(p-toluenesulfonyl)amino]-4-phenylbutanal 
• 875438-82-7 (3S)-[N-(3-methylbut-2-enyl)-N-(p-toluenesulfonyl)amino]-4-phenylbutyronitrile 
• 87982-79-4 R-(-)-1-phenyl-2-aminopentane 
• 139925-42-1 R-(+)-Prolintan 
• 662142-94-1 (S)-N-(1-azido-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide 
• 1254356-67-6 (2R,4R,5R)-2-benzyl-4-(methoxycarbonylmethyl)-1-(p-toluenesulfonyl)-5-vinylpiperidine 
• 1254356-69-8 (S,E)-8-acetoxy-4-aza-3-benzyl-4-(p-toluenesulfonyl)-7-[(triethyl)silyl]oct-6-enenitrile 
• 1254356-24-5 (S,E)-4-aza-3-benzyl-8-hydroxy-4-(p-toluenesulfonyl)-7-[(triethyl)silyl]oct-6-enal 
• 1254356-72-3 methyl (R,E,E)-6-aza-5-benzyl-10-hydroxy-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate 
• 1254356-25-6 methyl (R,E,E)-6-aza-5-benzyl-10-bromo-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate 
• 1254356-76-7 methyl (R,E,E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate 

Relevant articles and documents

Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization

A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2

Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations

An approach to 2,4,5-trisubstituted piperidines is reported, in which the key step is the Prins or carbonyl ene cyclisation of aldehydes of the type 1. Prins cyclisation catalysed by concentrated hydrochloric acid in CH 2Cl2 at -78 °C afforded good yields of two of the four possible diastereomeric piperidines, with the 4,5-cis product 7 predominating in a diastereomeric ratio of up to 94: 6. The diastereoselectivity of the cyclisation decreased as the 2-substituent increased in size, becoming unselective for very bulky 2-substituents. In contrast, cyclisation catalysed by MeAlCl2 in CH2Cl2 or CHCl3 at temperatures of between 20-60 °C, favoured the 4,5-trans diastereomer 8, in a diastereomeric ratio of up to 99: 1. The low-temperature cyclisations catalysed by HCl proceed under kinetic control via a mechanism involving the development of significant carbocationic character, in which the 4,5-cis cation is more stable than the 4,5-trans cation as a result of overlap with the neighbouring oxygen. The cyclisations catalysed by MeAlCl2 proceed under thermodynamic control, affording the product in which both the 4- and 5-substituents are equatorial.