86087-24-3

Basic information

• Product Name: (R)-(-)-3-Hydroxytetrahydrofuran
• Synonyms: (R)-(-)-TETRAHYDRO-3-FURANOL;(R)-(-)-3-HYDROXYTETRAHYDROFURAN;(R)-3-HYDROXYTETRAHYDROFURAN;(R)-(-)-3-HYDROXYTETRAHYDROFURANE;3-FURANOL, TETRAHYDRO-, (R);(R)-TETRAHYDROFURAN-3-OL ;(3R)-Tetrahydrofuran-3-ol;(3R)-Tetrahydrofuran-3α-ol
• CAS NO: 86087-24-3
• Molecular Formula: C4H8O2
• Molecular Weight: 88.11
• EINECS: 1308068-626-2
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;chiral;Tetrahydrofuran Series;Furans;Building Blocks for HIV Protease InhibitorsChiral Building Blocks;Cell Signaling Enzymes;Heterocyclic Building Blocks;HIV Protease Reagents&Envelope Proteins
• Mol File: 86087-24-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 181 °C(lit.)
• Flash Point: 180 °F
• Appearance: Clear colorless/Liquid
• Density: 1.097 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.255mmHg at 25°C
• Refractive Index: n20/D 1.45(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 14.49±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-3-Hydroxytetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-3-Hydroxytetrahydrofuran(86087-24-3)
• EPA Substance Registry System: (R)-(-)-3-Hydroxytetrahydrofuran(86087-24-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 86087-24-3(Hazardous Substances Data)

Usage

Description

(R)-(-)-3-Hydroxytetrahydrofuran is a chiral organic compound characterized by its unique four-membered ring structure and a hydroxyl functional group. It is a versatile intermediate in the synthesis of various pharmaceutical agents and other organic compounds. Its colorless to light yellow liquid form makes it suitable for use in chemical reactions without imparting color to the final product.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-3-Hydroxytetrahydrofuran is used as a chemical reactant for the synthesis of pharmaceutical agents. It plays a crucial role in the production of Empagliflozin, a medication used for the treatment of type 2 diabetes.
Used in HIV Treatment:
(R)-(-)-3-Hydroxytetrahydrofuran may be used as a building block in the synthesis of potent HIV protease inhibitors. These inhibitors are essential in the development of antiretroviral drugs that help manage and treat HIV/AIDS by inhibiting the replication of the virus within the host cells.

InChI:InChI=1/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m1/s1

Upstream product

• 1708-29-8 2,5-dihydrofuran 
• 145873-44-5 4-chloro-3-hydroxy-1-butanol 
• 125605-10-9 (3R)-4-chloro-1,3-butanediol 
• 22929-52-8 tetrahydrofuran-3-one 
• 27999-96-8 (+/-)-tetrahydrofuran-3-yl acetate 
• 778-29-0 but-3-enyl 4-methylbenzenesulfonate 
• 453-20-3 3-Hydroxytetrahydrofuran 
• 108-05-4 vinyl acetate 
• 42890-76-6 (S)-1,2,4-butanetriol 
• 106-97-8 n-butane 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 1191-99-7 2,3-dihydro-2H-furan 
• 1358604-08-6 (R)-tetrahydrofuran-3-yl 4-nitrobenzoate 

Downstream Products

• 1358604-08-6 (R)-tetrahydrofuran-3-yl 4-nitrobenzoate 
• 1364632-45-0 [(3S)-tetrahydrofuran-3-yl]hydrazine hydrochloride 
• 915095-89-5 (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene 
• 1586046-13-0 (R)-2-(2,6-difluoro-4-((tetrahydrofuran-3-yl)oxy)phenyl)thiazole-4-carboxylic acid 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 

Relevant articles and documents

Methodology Development in Directed Evolution: Exploring Options when Applying Triple-Code Saturation Mutagenesis

Directed evolution of stereo- or regioselective enzymes as catalysts in asymmetric transformations is of particular interest in organic synthesis. Upon evolving these biocatalysts, screening is the bottleneck. To beat the numbers problem most effectively, methods and strategies for building “small but smart” mutant libraries have been developed. Herein, we compared two different strategies regarding the application of triple-code saturation mutagenesis (TCSM) at multiresidue sites of the Thermoanaerobacter brockii alcohol dehydrogenase by using distinct reduced amino-acid alphabets. By using the synthetically difficult-to-reduce prochiral ketone tetrahydrofuran-3-one as a substrate, highly R- and S-selective variants were obtained (92–99 % ee) with minimal screening. The origin of stereoselectivity was provided by molecular dynamics analyses, which is discussed in terms of the Bürgi–Dunitz trajectory.

THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TETRAHYDRO-3-FURANYL] OXY]PHENYL] METHYL]PHENYL]-, (1S) AND ITS CRYSTALLINE FORMS THEREOF.

The present invention relates to process for the preparation of D-glucitol, 1,5- anhydro-l-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl] methyl]phenyl]-, (1S) formula- 1 and its crystalline forms thereof.

A pharmaceutical intermediates (S)-3 - hydroxy tetrahydrofuran preparation method (by machine translation)

The invention provides a pharmaceutical intermediate (S)- 3 - hydroxy tetrahydrofuran preparation method. The method other than racemic 1, 2, 4 - butanetriol as raw materials synthesis of racemic 3 - hydroxy tetrahydrofuran, then esterification of racemic tetrahydrofuran-yl - 3 - fatty acid ester. By lipase hydrolysis in the racemic mixture of (R)- tetrahydrofuran-based - 3 - fatty acid ester after, in in the hydrolysis product under the condition of separating, using the mitsunobu reaction will be hydrolyzed to obtain the of (R)- 3 - hydroxy tetrahydrofuran is converted into (S)- tetrahydrofuran-based - 3 - carboxylic acid ester, finally under alkaline condition all of the tetrahydrofuran ester hydrolyzed to obtain the final product (S)- 3 - hydroxy tetrahydrofuran. (by machine translation)