3-Hydroxytetrahydrofuran 98% supplier in China CAS NO.453-20-3

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1. Introduction of 3-Hydroxytetrahydrofuran

3-Hydroxytetrahydrofuran (3-OH THF) is a colorless liquid with a normal boiling point of 179 °C and boiling at 88?89 °C at 17 mmHg, with density (1.087 g/cm3 at 19 °C)similar to that of water. 3-OH THF is a useful pharmaceutical intermediate. The chiral (absolute configuration S) version of this compound is an intermediate to launched retroviral drugs

2. Properties of 3-Hydroxytetrahydrofuran

Molecular Weight 88.10512 [g/mol]
Molecular Formula C4H8O2
XLogP3-AA -0.4
H-Bond Donor 1
H-Bond Acceptor 2
Exact Mass 88.052429
MonoIsotopic Mass 88.052429
Topological Polar Surface Area 29.5
Heavy Atom Count 6
Complexity 44.8
Undefined Atom Stereocenter Count 1 
Covalently-Bonded Unit Count 1
Feature 3D Acceptor Count 2
Feature 3D Donor Count 1
Feature 3D Ring Count 1
Effective Rotor Count 1
Conformer Sampling RMSD 0.4
CID Conformer Count 2
 

3. Structure descriptors of 3-Hydroxytetrahydrofuran

IUPAC Name: oxolan-3-ol

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

InChIKey: XDPCNPCKDGQBAN-UHFFFAOYSA-N

Canonical SMILES : C1COCC1O

4. Synthesis

Chiral 3-hydroxytetrahydrofuran (both (S)- and (R)-forms) has been synthesized in high enantiomeric purity from (S)- and (R)-1,2,4-butanetriol, respectively, obtained from chiral feedstocks. Thus, the chiral (S)-1,2,4-butanetriol intermediate was cyclized to chiral (S)-3-hydroxytetrahydrofuran in the presence of p-toluenesulfonic acid (PTSA) catalyst at temperatures of 180?220 °C. Similarly, (S)-3-hydroxytetrahydrofuran was prepared in 95.8% optical purity from L-malic acid via an esterification-reduction-cyclodehydration sequence. 3-hydroxytetrahydrofuran has been synthesized via hydroboration of 2,3- and 2,5-dihydrofuran employing various borane reagents and chiral 3-hydroxytetrahydrofurans have also been prepared by catalytic asymmetric hydroboration of 2,3- and 2,5-dihydrofurans with a borane in the presence of a homogeneous chiral platinum complex, followed by oxidation.[8] Racemic 3-hydroxytetrahydrofuran may be prepared in analogous fashion from racemic butanetriol, employing PTSA catalyst for the dehydrocyclization. Alternatively, 1,2,4-butanetriol may be converted to 3-hydroxytetrahydrofuran by treating with ethylene carbonate, followed by pyrolysis of the resulting carbonate ester.

5. Applications

3-Hydroxytetrahydrofuran is an intermediate to the AIDS drugs amprenavir and fosamprenavir.Additionally, 3-OH THF has been an intermediate to developmental drug substances, such as chemotherapy agents. For example, reaction of phosphorus pentasulfide with 3-hydroxytetrahydrofuran has been used in the synthesis of bis(O,O-di(tetrahydrofuran-3-yl)hydrogen dithiophosphate)platinum(II), a cisplatin analog.3-hydroxytetrahydrofuran may be converted into a range of tetrahydrofuran derivatives, many of which also serve as intermediates to compounds of pharmaceutical interest. For example, tetrahydrofuran-3-one (3-ketotetrahydrofuran) and 3-aminotetrahydrofuran have been synthesized from 3-hydroxytetrahydrofuran and used in pharmaceutical syntheses. Additionally, additive amounts (0.05-0.15 weight %) of the nitrate ester manufactured by sulfuric acid-nitric acid nitration of 3-hydoxytetrahydrofuran have been found to increase the quality (cetane number) of diesel fuel.