103745-07-9

Basic information

• Product Name: (R)-2-HYDROXYBUTYL P-TOSYLATE,98+%
• Synonyms: (R)-2-HYDROXYBUTYL P-TOSYLATE,98+%;(R)-2-Hydroxybutyl p-tosylate;R-1-(4-Methylbenzenesulfonate)-1,2-Butanediol
• CAS NO: 103745-07-9
• Molecular Formula: C₁₁H₁₆O₄S
• Molecular Weight: 244.30734
• Mol File: 103745-07-9.mol

Chemical Properties

• Boiling Point: 357.23°C (rough estimate)
• Appearance: /
• Density: 1.2976 (rough estimate)
• Refractive Index: 1.5220 (estimate)
• CAS DataBase Reference: (R)-2-HYDROXYBUTYL P-TOSYLATE,98+%(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-HYDROXYBUTYL P-TOSYLATE,98+%(103745-07-9)
• EPA Substance Registry System: (R)-2-HYDROXYBUTYL P-TOSYLATE,98+%(103745-07-9)

Safety Data

• Hazardous Substances Data: 103745-07-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-2-HYDROXYBUTYL P-TOSYLATE,98+% is used as a protecting group for alcohols in organic synthesis for [application reason] its ability to undergo various chemical reactions, such as nucleophilic substitution, to produce a wide range of other organic compounds.
Used in Pharmaceutical Production:
(R)-2-HYDROXYBUTYL P-TOSYLATE,98+% is used as a valuable reagent in the production of pharmaceuticals and fine chemicals for [application reason] its high purity, stability, and reactivity, which contribute to the creation of precise and reliable pharmaceutical products.
Used in Research Applications:
(R)-2-HYDROXYBUTYL P-TOSYLATE,98+% is used as a research compound for [application reason] its suitability in providing accurate and dependable results in scientific investigations and experiments.

Upstream product

• 103745-05-7 2-butanoyloxybutyl p-toluenesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 40348-66-1 (R)-1,2-butanediol 
• 141783-42-8 (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane 

Downstream Products

• 589-98-0 (R)-octan-3-ol 

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.

C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Application and Synthesis of Naturally Occuring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly.In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or threo stereochemistry starting from trans or cis epoxy alcohols.Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occuring (S,S)-2,3-octanediol and (R,R)-muricatacin.The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides.The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols.This methodology has been applied to the asymmetric synthesis of naturally occuring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols

2,3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones