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
• Article Data: 12

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

General Description

(+/-)-2-Hydroxy-3-buten-1-yl tosylate is a chemical compound commonly used in organic synthesis and as a reagent in chemical reactions. It is a tosylate ester of 2-hydroxy-3-buten-1-ol, which means it contains a tosyl group (p-toluenesulfonyl group) attached to the hydroxyl group of the alcohol. (+/-)-2-Hydroxy-3-buten-1-yl tosylate is often used as a leaving group in substitution reactions, where the tosyl group is displaced by a nucleophile. It is also used as a protecting group for alcohols, where the tosyl group temporarily blocks the reactivity of the hydroxyl group, allowing other parts of the molecule to undergo chemical reactions. It is a versatile compound with various applications in organic chemistry.

Upstream product

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

Downstream Products

• 133095-74-6 (S)-2-hydroxy-3-buten-1-yl p-tosylate 
• 138249-07-7 2-hydroxy-(2R)-3-butenyl-4-methyl-1-benzenesulfonate 
• 138458-26-1 (R)-1-tosyloxy-2-acetyloxy-3-butene 
• 138332-14-6 (S)-1-tosyloxy-2-acetyloxy-3-butene 
• 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 
• 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 
• 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.

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.

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.