138332-13-5

Basic information

• Product Name: (+/-)-2-Hydroxy-3-buten-1-yl tosylate
• Synonyms: (+/-)-2-Hydroxy-3-buten-1-yl tosylate
• CAS NO: 138332-13-5
• Molecular Formula: C₁₁H₁₄O₄S
• Molecular Weight: 242.29146
• Mol File: 138332-13-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+/-)-2-Hydroxy-3-buten-1-yl tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2-Hydroxy-3-buten-1-yl tosylate(138332-13-5)
• EPA Substance Registry System: (+/-)-2-Hydroxy-3-buten-1-yl tosylate(138332-13-5)

Safety Data

• Hazardous Substances Data: 138332-13-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(+/-)-2-Hydroxy-3-buten-1-yl tosylate is used as a reagent in organic synthesis for its ability to act as a leaving group in substitution reactions. The tosyl group is displaced by a nucleophile, allowing for the formation of new chemical bonds and the creation of a wide range of organic compounds.
Used as a Protecting Group for Alcohols:
In the field of organic chemistry, (+/-)-2-Hydroxy-3-buten-1-yl tosylate serves as a protecting group for alcohols. The tosyl group temporarily blocks the reactivity of the hydroxyl group, enabling other parts of the molecule to undergo chemical reactions without interference from the alcohol group. This selective protection is crucial for the synthesis of complex organic molecules and the development of pharmaceuticals and other chemical products.
Used in Chemical Reactions:
(+/-)-2-Hydroxy-3-buten-1-yl tosylate is also utilized in various chemical reactions due to its unique properties as a tosylate ester. Its ability to participate in substitution reactions and protect alcohol groups makes it a valuable tool for chemists working on the synthesis and modification of organic compounds across different industries.

Upstream product

• 497-06-3 3,4-butenediol 
• 104-15-4 toluene-4-sulfonic acid 
• 1122-58-3 dmap 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 881383-22-8 methyl 1-(tosylox)but-3-en-2-yl malonate 
• 811867-61-5 Toluene-4-sulfonic acid 2-(2-bromo-6-vinyl-phenoxy)-but-3-enyl ester 
• 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 
• 913824-83-6 2-(2-Methoxy-6-vinylphenoxy)-3-butenyl 4-methylbenzenesulfonate 
• 913825-03-3 2-{2-bromo-4-fluoro-6-[(1E)-prop-1-enyl]phenoxy}but-3-enyl 4-methylbenzenesulfonate 
• 206257-83-2 (R)-1-p-toluenesulfonyloxy-3-butene-2-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 783322-43-0 1-phenylsulfanyl-2(S)-3-buten-2-ol 
• 881383-26-2 2-((tert-butyldimethylsilyl)oxy)but-3-en-1-yl 4-methylbenzenesulfonate 
• 138458-26-1 (R)-1-tosyloxy-2-acetyloxy-3-butene 
• 138249-06-6 (±)-2-acetoxybut-3-enyl tosylate 

Relevant articles and documents

CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO

The invention relates to inhibitors of calcium-dependent protein kinase 1 (CDPK1) and pharmaceutical preparations thereof. The invention further relates to methods of treatment of parasitic infections, such as T. gondii, P. falciparum, C. hominis, or C. parvum infections, using the novel inhibitors of the invention.

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.

Enantioselective synthesis of cyclic, quaternary oxonitriles

Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition-elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while selectively forming a new quaternary center with enantiomeric ratios typically greater than 9:1. The overall alkylation strategy addresses the challenge of enantioselectively generating hindered, quaternary centers while simultaneously installing ketone, nitrile, and olefin functionalities.

Further improvements of the dibutyl tin oxide-catalyzed regioselective diol tosylation

In this Letter, we report that selective monotosylation of a 1,2-diol is possible using only 0.1 mol % of Bu2SnO. More interestingly, we found that the corresponding tin acetal 3b gave faster conversions and more reproducible reaction times. Moreover, the loading of this catalyst could be as low as 0.05-0.005 mol %.

Synthesis and mutagenesis of the butadiene-derived N3 2′-deoxyuridine adducts

1,3-Butadiene is a known carcinogen and mutagen that acts through a variety of metabolic intermediates that react with DNA, forming stable and unstable lesions on dG, dA, dC, and dT. The N3 2′-deoxyuridine adducts are a highly stable, stereoisomeric mixture of adducts derived from the reaction of cytosine with the monoepoxide metabolite of butadiene, followed by spontaneous deamination. In this study, the phosphoramidites and subsequent oligodeoxynucleotides containing the N3 2′-deoxyuridine adducts have been constructed and characterized. Using a single-stranded shuttle vector DNA, the mutagenic potential of these adducts has been tested following replication in mammalian cells. Replication past the N3 2′-deoxyuridine adducts was found to be highly mutagenic with an overall mutation yield of ～97%. The major mutations that were observed were C to T transitions and C to A transversions. In vitro, these adducts posed a complete block to both the Klenow fragment of Escherichia coli polymerase I and polymerase ε, while these lesions significantly blocked polymerase δ. These data suggested a possible involvement of bypass polymerases in the in vivo replication of these lesions. Overall, these findings indicate that the N3 2′-deoxyuridine adducts are highly mutagenic lesions that may contribute to butadiene-mediated carcinogenesis.

Synthesis of methyl 2-oxo-5-vinyl-2,5-tetrahydrofuran-3-carboxylate

A synthesis of methyl 2-oxo-5-vinyl-tetrahydrofuran-3-carboxylate involving five synthetic steps from commercially available 3,4-dihydroxybutene is reported.

New synthesis of sn-1,2- and sn-2,3-O-diacylglycerols application to the synthesis of enantiopure phosphonates analogous to triglycerides: A new class of inhibitors of lipases

Phosphonate compounds mimic the first transition state occurring during enzymatic carboxyester hydrolysis of natural substrates by forming a covalent bond with the catalytic serine. However, until now the organophosphorus compounds used in the inhibition studies more or less resembled a natural triglyceride substrate. In order to elucidate the interfacial activation and the mechanism of action of lipases, specific inhibitors need to be prepared. To achieve this goal, enantiomerically pure sn-1,2- and sn-2,3O- didecanoylglycerol compounds were prepared - starting from a C-4 chiral synthon, 3-buten-1,2-diol - and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be investigated as inhibitors of Human Pancreatic Lipase (HPL) and Human Gastric Lipase (HGL) using the monomolecular film technique.

Method for purification of alcohols

A method for the purification of alcohols from organic soluble impurities has been discovered comprising treating the crude alcohol with a cyclic anhydride followed by an aqueous base and extracting the corresponding half-ester into aqueous solution leaving the impurities in organic solution. This method is particularly useful for the separation of chiral, nonracemic alcohols from the corresponding antipodal ester (the mixture resulting from an enzymatic kinetic resolution) because the separation is non-chromatographic and the enantiomeric integrity of the products is maintained.

Synthesis of enantiomerically pure 3-butene-1,2-diol derivatives via a Sharpless asymmetric epoxidation route

A short enantiospecific synthesis of the butenediol monotosylates (1,2), the epoxybutanediol monotosylates (3,4) and the epoxybutenes (5,6) is described.

Method of intercoversion of enantiomers of acyclic 1,2-dihydroxy-3-alkenes

In accordance with the present invention, a method for the interconvertion of the enantiomers of acyclic 1,2-dihydroxy-3-alkenes or for converting either enantiomer of acylic 1,2-dihydroxy-3-alkenes to the corresponding antipodal 1-hydroxy-2-alkoxy-3-alke