79107-75-8

Basic information

• Product Name: (S)-(+)-3-HYDROXYTETRAHYDROFURAN
• Synonyms: (S)-TETRAHYDROFURAN-3-OL;(S)-(+)-3-HYDROXY TETAHYDRO FURAN;(S)-(+)-3-HYDROXYTETRAHYDROFURANE;3-FURANOL, TETRAHYDRO-, (S);(3S)-Tetrahydrothiophen-3-ol;(3S)-Tetrahydrothiophene-3-ol
• CAS NO: 79107-75-8
• Molecular Formula: C4H8O2
• Molecular Weight: 88.11
• Mol File: 79107-75-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 80 °C15 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 1.103 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.255mmHg at 25°C
• Refractive Index: n20/D 1.45(lit.)
• PKA: 14.43±0.20(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: (S)-(+)-3-HYDROXYTETRAHYDROFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-HYDROXYTETRAHYDROFURAN(79107-75-8)
• EPA Substance Registry System: (S)-(+)-3-HYDROXYTETRAHYDROFURAN(79107-75-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 79107-75-8(Hazardous Substances Data)

Usage

General Description

(S)-(+)-3-Hydroxytetrahydrofuran is a chemical compound belonging to the category of organic compounds known as tetrahydrofurans. It is a specific isomer of hydroxytetrahydrofuran, with "S" indicating the specific arrangement of atoms in the molecule. The compound exists in a liquid form and has applications in various aspects of chemical and biological research. Depending on its context and usage, it may behave as an organooxygen compound and a polar solvent in different reactions. The compound is also known for its potential use in the production of certain pharmaceuticals and other organic compounds, due to its characteristics as a chiral, or 'handed', molecule.

InChI:InChI=1/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m0/s1

Upstream product

• 1120-59-8 2,3-dihydrothiophene 
• 1003-04-9 Tetrahydrothiophen-3-one 
• 61847-07-2 (S)-(+)-4-bromo-1,2-epoxybutane 
• 147949-22-2 3(S)-(tetrahydropyranyloxy)tetrahydrothiophene 

Relevant articles and documents

Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots

A whole spectrum of biocatalysts for asymmetric reduction of prochiral ketones is well known including the Daucus carota root. However, this type of reaction is still challenging when pro-chiral ketones present low level of asymmetry, like heterocyclic ketones. In this work, 4,5-dihydro-3(2H)-thiophenone (1), 2-methyltetrahydrofuran-3-one (2), N-Boc-3-pyrrolidinone (3), 1-Z-3-pyrrolidinone (4) and 1-benzyl-3-pyrrolidinone (5) were studied in order to obtain the respective enantioselective heterocyclic secondary alcohols. Except for 5, the corresponding alcohols were obtained in high values of conversion and with high selectivity. In order to circumvent the low isolated yield of the corresponding chiral alcohol from 2, we observed that the use of carrots in the absence of water is feasible. Addition of co-solvents was needed to the water-insoluble ketones 3 and 4. Comparatively, baker’s yeast was used for bio reductions of 1, 3 and 4. And in terms of conversion, selectivity and work-up, the use of carrots were a more efficient biocatalyst, as well as a viable method for obtaining 5-member heterocyclic secondary alcohols.

Highly enantioselective reduction of a small heterocyclic ketone: Biocatalytic reduction of tetrahydrothiophene-3-one to the corresponding (R)-Alcohol

By leveraging enzyme evolution technologies, the enantioselectivity of a KetoREDuctase (KRED) towards the nearly spatially symmetrical ketone tetrahydrothiophene-3-one was increased from 63% ee to 99.3% ee. The biocatalytic process gives (R)-tetrahy- drothiophene-3-ol in one step from a commodity chemical and supplants the original multistep hazardous processes starting from the chiral pool. The biocatalytic process has been successfully scaled to 100 kg.

HIV protease inhibitors

Oligopeptide analogs are described. These compounds are useful in the inhibition of HIV protease, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition