138249-06-6

Basic information

• Product Name: (±)-2-acetoxybut-3-enyl tosylate
• Synonyms: (±)-2-acetoxybut-3-enyl tosylate
• CAS NO: 138249-06-6
• Molecular Weight: 284.333
• Mol File: 138249-06-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (±)-2-acetoxybut-3-enyl tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-2-acetoxybut-3-enyl tosylate(138249-06-6)
• EPA Substance Registry System: (±)-2-acetoxybut-3-enyl tosylate(138249-06-6)

Safety Data

• Hazardous Substances Data: 138249-06-6(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 108-24-7 acetic anhydride 
• 138332-13-5 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate 

Downstream Products

• 138249-07-7 2-hydroxy-(2R)-3-butenyl-4-methyl-1-benzenesulfonate 
• 138332-14-6 (S)-1-tosyloxy-2-acetyloxy-3-butene 
• 133095-74-6 (S)-2-hydroxy-3-buten-1-yl p-tosylate 
• 206257-83-2 (R)-1-p-toluenesulfonyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 

Relevant articles and documents

Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent

We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.

Protected hydroxy method for alcohol-ester separation

A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched alcohol and an enantiomerically enriched ester. The process includes the steps of: (a) contacting the mixture with a reagent capable of reacting with the hydroxy function of the alcohol, without the loss of optical purity, so as to produce a second mixture containing a base stable derivative of the enantiomerically enriched alcohol and the unreacted ester; (b) contacting the second mixture with a base capable of reacting with the ester so as to produce a third mixture containing a compound more volatile than the base stable derivative of the alcohol; (c) removing the volatile compound from the third mixture; and (d) converting the base stable derivative of the alcohol back to the enantiomerically enriched alcohol, without the loss of optical purity.