152752-38-0

Basic information

• Product Name: 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate
• Synonyms: 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate
• CAS NO: 152752-38-0
• Molecular Weight: 286.349
• Mol File: 152752-38-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate(152752-38-0)
• EPA Substance Registry System: 2-hydroxy-3-allyloxypropyl 4-toluenesulfonate(152752-38-0)

Safety Data

• Hazardous Substances Data: 152752-38-0(Hazardous Substances Data)

Upstream product

• 123-34-2 3-allyloxy-1,2-propanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-92-3 Allyl glycidyl ether 
• 104-15-4 toluene-4-sulfonic acid 
• 5593-70-4 titanium (IV) butoxide 
• 3087-39-6 titanium(IV) tert-butoxide 
• 546-68-9 titanium(IV)isopropoxide 

Downstream Products

• 128572-87-2 Acetic acid (S)-1-allyloxymethyl-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 128495-90-9 Toluene-4-sulfonic acid (R)-3-allyloxy-2-hydroxy-propyl ester 
• 95043-56-4 (-)-3-(allyloxy)-1,2-epoxypropane 
• 95043-55-3 (+)-3-(allyloxy)-1,2-epoxypropane 
• 128495-89-6 3-(allyloxy)-2-acetoxypropyl p-toluenesulfonate 

Relevant articles and documents

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

Enzymes in Organic Synthesis: Synthesis of Highly Enantiomerically Pure 1,2-Epoxy Aldehydes, Epoxy Alcohols, Thiirane, Aziridine, and Glyceraldehyde 3-Phosphate

This paper describes a chemoenzymatic procedure for the synthesis of (R)- and (S)-glycidaldehyde diethyl acetal (4 and 5). 2-Acetoxy-3-chloropropanal diethyl acetal (1c) was enantioselectively hydrolyzed by LP-80 lipase to give (S)-3-chloro-2-hydroxypropanal diethyl acetal (2c) and the unreacted acetate (3c), both in >95percent calculated yield and >98percent ee.Both products were subsequently converted to epoxides 4 and 5, respectively.Resolutions of 2-acetoxy-1-(benzyloxy)-3-chloropropane (11a) and 3-(allyloxy)-2-acetoxypropyl p-toluenesulfonate (14b) were similarly carried out to give the corresponding optically active 2-hydroxy and 2-acetoxy derivatives in 90percent and >95percent ee.These products were subsequently converted to the corresponding 1,2-epoxides.Nucleophilic opening of epoxide 4 was exemplified by the syntheses of (R)-3-azido-2-hydroxypropanal and D-glyceraldehyde 3-phosphate.Conversion of the chiral epoxides to thiirane and aziridine was also described.