285-69-8

Usage

Uses

Used in Polymer Industry:
3,4-Epoxytetrahydrofuran is used as a reagent for the production of various degradable polymers from epoxides. This application is particularly significant due to the growing demand for environmentally friendly materials that can break down over time, reducing the impact of plastic waste on the environment.
The use of a versatile dinuclear chromium catalyst in the process allows for the creation of polymers with specific properties tailored to various end-use applications, such as packaging materials, agricultural films, and biodegradable medical devices.

InChI:InChI=1/C4H6O2/c1-3-4(6-3)2-5-1/h3-4H,1-2H2/t3-,4+

Synthetic route

2,5-dihydrofuran (1708-29-8) → 3,4-epoxytetrahydrofuran (285-69-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃;	84.6%
With mCPHA In dichloromethane at 0 - 20℃;	84.6%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Heating;	71%

trans-4-chloro-tetrahydro-furan-3-ol → 3,4-epoxytetrahydrofuran (285-69-8)

Conditions	Yield
With copper(I) oxide; diisopropylbenzene
With sodium hydroxide
With calcium hydroxide; water

3,4-epoxytetrahydrofuran (285-69-8) → trans-4-amino-3-hydroxytetrahydrofuran (144870-96-2)

Conditions	Yield
With ammonium hydroxide at 85℃; for 0.5h; microwave irradiation;	100%
With ammonium hydroxide In isopropyl alcohol at 80℃; for 12h;	95%
With ammonia In water; isopropyl alcohol at 80℃; for 12h;	95%
With ammonium hydroxide
With ammonium hydroxide at 100℃; for 14h;

3,4-epoxytetrahydrofuran (285-69-8) → 4-amino-3-hydroxytetrahydrofuran (144870-96-2)

Conditions	Yield
With ammonium hydroxide In isopropyl alcohol at 80℃; for 15h;	100%
With ammonia; water In isopropyl alcohol at 80℃; for 18h;	96.8%
With ammonia In water; isopropyl alcohol at 80℃; for 18h;	96.8%

3,4-epoxytetrahydrofuran (285-69-8) + 4’-hydroxy-2’,6’-dimethyl-3-biphenylcarbaldehyde (805250-31-1) → 4′-(((3R,4R)/(3S,4S)-4-hydroxytetrahydrofuran-3-yl)oxy)-2',6'-dimethylbiphenyl-3-carbaldehyde

Conditions	Yield
With potassium carbonate In ethanol at 100℃; for 1.5h; Microwave irradiation;	100%
With potassium carbonate In ethanol at 100℃; for 1.5h; Inert atmosphere; Microwave irradiation;	100%

3,4-epoxytetrahydrofuran (285-69-8) + 4-bromo-phenol (106-41-2) → trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; caesium carbonate In 1,4-dioxane for 18h; Reflux; Inert atmosphere;	100%

3,4-epoxytetrahydrofuran (285-69-8) + carbon dioxide (124-38-9) → tetrahydrofuro[3,4-d]1,3-dioxolan-2-one

Conditions	Yield
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 12h; chemoselective reaction;	98%
With C68H105N2O5YZn; tetrabutylammomium bromide In butanone at 70℃; under 7600.51 Torr; for 24h; Temperature; Autoclave;	92%
With C32H24Al2Cl8N2O6*2C4H8O; tetrabutylammomium bromide In neat (no solvent) at 85℃; under 7500.75 Torr; for 40h; Schlenk technique;	89%

3,4-epoxytetrahydrofuran (285-69-8) + tert-butyl 4-(2-fluoro-4-hydroxyphenyl)piperazine-1-carboxylate (501126-38-1) → tert-butyl 4-(2-fluoro-4-((4-hydroxytetrahydrofuran-3-yl)oxy)phenyl)piperazine-1-carboxylate

Conditions	Yield
With caesium carbonate In 1,4-dioxane at 100℃; for 16h;	98%

3,4-epoxytetrahydrofuran (285-69-8) + 1-Chloro-4-iodobenzene (637-87-6) + benzene 1,3,5-triyl triformate → C11H10Cl2O3

Conditions	Yield
With aluminum (III) chloride; palladium diacetate; triethylamine; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 85℃; for 20h; Sealed tube; Inert atmosphere;	96%

3,4-epoxytetrahydrofuran (285-69-8) + t-butylsulfonamide (34813-49-5) → (+/-)-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]-tert-butylsulfonamide

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 96h;	95%

3,4-epoxytetrahydrofuran (285-69-8) + trimethylsilylazide (4648-54-8) → ((3R,4S)-4-azidotetrahydrofuran-3-yloxy)trimethylsilane (190792-68-8)

Conditions	Yield
With (1R,2R)-salen catalyst In diethyl ether at 25℃;	93%
With (R,R)-(salen)Cr(III) 1.) Et2O, 15 min, 2.) Et2O, RT, 18 h; Multistep reaction;
With (R,R)-Cr(N2(CH)2CHCH(CH2)4)(OC6H2(t-Bu)2)2N3 for 24h; Ambient temperature; further reagent: chiral (salen)Cr(III)Cl complex;	97 % Turnov.
chiral Cr(salen) In various solvent(s) at 20℃; for 18h; Ring cleavage;

3,4-epoxytetrahydrofuran (285-69-8) + tert.-butyl lithium (594-19-4) → 4,4-dimethyl-3-methylenepentane-1,2-diol

Conditions	Yield
In tetrahydrofuran; pentane at -78 - 20℃; for 1h;	93%
In tetrahydrofuran at -78 - 25℃;	93%

3,4-epoxytetrahydrofuran (285-69-8) + carbon monoxide (201230-82-2) → 3,6-dioxabicyclo[3.2.0]heptan-7-one (1309803-08-4)

Conditions	Yield
With dicobalt octacarbonyl; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) In 1,2-dimethoxyethane at 70℃; under 1034.32 - 25858.1 Torr; for 16h; Inert atmosphere;	93%
With dicobalt octacarbonyl; tetraphenylporphyrinchromium(III) chloride In tetrahydrofuran at 70℃; under 25858.1 Torr; for 16h; Inert atmosphere;	91%

3,4-epoxytetrahydrofuran (285-69-8) + sec.-butyllithium (598-30-1) → 4-methyl-3-methylenehexane-1,2-diol

Conditions	Yield
In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	92%
In tetrahydrofuran at -78 - 25℃;	92%

3,4-epoxytetrahydrofuran (285-69-8) + trimethylsulphonium iodide (2181-42-2) → tetrahydrofuran-4-methylidene-3-ol (390381-85-8)

Conditions	Yield
Stage #1: trimethylsulphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.5h; Stage #2: 3,4-epoxytetrahydrofuran In tetrahydrofuran; hexane at -10 - 20℃; Further stages.;	92%

3,4-epoxytetrahydrofuran (285-69-8) + bromobenzene (108-86-1) → (3S,4R)-4-phenyltetrahydrofuran-3-ol (130871-09-9)

Conditions	Yield
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II); bis(η5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride; triethylamine hydrochloride at 20℃; for 12h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction;	91%

3,4-epoxytetrahydrofuran (285-69-8) + trimethylsilylazide (4648-54-8) → (3R,4S)-3-azido-4-trimethylsiloxytetrahydrofurane

Conditions	Yield
With (1S,2S)-salen catalyst In diethyl ether at 25℃;	90%

3,4-epoxytetrahydrofuran (285-69-8) + n-butyllithium (109-72-8, 29786-93-4) → 3-methyleneheptane-1,2-diol

Conditions	Yield
In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	90%
In tetrahydrofuran; hexane at -78 - 25℃; for 1h;	90%

3,4-epoxytetrahydrofuran (285-69-8) + dimethyl amine (124-40-3) → trans-3-(dimethylamino)-4-hydroxytetrahydrofuran

Conditions	Yield
In water at 50 - 55℃;	90%

3,4-epoxytetrahydrofuran (285-69-8) + tert-butyl N-(6-aminohexyl)carbamate (51857-17-1) → OC4H6OHHNC6H12NHCOOC4H9

Conditions	Yield
In water at 105℃; microwave irradiation;	90%

3,4-epoxytetrahydrofuran (285-69-8) + N-(tert-butoxycarbonyl)-1,7-heptanediamine (99733-18-3) → OC4H6OH2NC7H14NHCOOC4H9

Conditions	Yield
In water at 105℃; microwave irradiation;	90%

3,4-epoxytetrahydrofuran (285-69-8) + carbon dioxide (124-38-9) → (3aRS,7aSR)-tetrahydrofuro[3,4-d][1,3]dioxol-2-one (1379481-94-3)

Conditions	Yield
With C21H12Cl6NO4V; tetrabutylammomium bromide In neat (no solvent) at 85℃; under 7500.75 Torr; for 18h;	89%
With C80H128La2N2O10*2C4H8O; tetrabutylammomium bromide at 100℃; under 7500.75 Torr; for 40h;	89%
With (2-hydroxyphenyl)diphenyl(propyl)phosphonium iodide In neat (no solvent) at 80℃; under 18751.9 Torr; for 24h; Autoclave;	82%

3,4-epoxytetrahydrofuran (285-69-8) + cyclopropylmagnesium bromide (23719-80-4) → (±)-trans-4-cyclopropyltetrahydrofuran-3-ol

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	87.3%

3,4-epoxytetrahydrofuran (285-69-8) + 1-amino-4-[(tert-butyloxycarbonyl)amino]butane (68076-36-8) → OC4H6OHHNC4H8NHCOOC4H9

Conditions	Yield
In water at 105℃; microwave irradiation;	87%

3,4-epoxytetrahydrofuran (285-69-8) + CH2Cl2:MeOH + 1-[(4-chlorophenyl)methyl]piperazine (23145-88-2) → (+/-)-trans-4-[4-(4-chlorobenzyl)-piperazin-1-yl]-tetrahydrofuran-3-ol

Conditions	Yield
With ammonium hydroxide In ethanol; dichloromethane	87%

3,4-epoxytetrahydrofuran (285-69-8) + 2,4,6-triisopropylbenzene sulfonamide (105536-22-9) → (+/-)-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]-2,4,6-triisoproplybenzenesulfonamide

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 96h;	86%

3,4-epoxytetrahydrofuran (285-69-8) + 5-tert-butoxycarbonylamino-1-aminopentane (51644-96-3) → OC4H6OHHNC5H10NHCOOC4H9

Conditions	Yield
In water at 105℃; microwave irradiation;	85%

3,4-epoxytetrahydrofuran (285-69-8) + 4‐(tert‐butoxycarbonylamino)benzylamine (220298-96-4) → OC4H6OH2NC7H6NHCOOC4H9

Conditions	Yield
In water at 105℃; microwave irradiation;	85%

3,4-epoxytetrahydrofuran (285-69-8) → C4H6O4S

Conditions	Yield
With C25H20AlCl6NO4; sulfur dioxide; tetrabutylammomium bromide In acetonitrile at 70℃; for 16h; Flow reactor; chemoselective reaction;	85%

3,4-epoxytetrahydrofuran (285-69-8) + iodobenzene (591-50-4) → 3-hydroxy 4-phenylselenotetrahydrofuran

Conditions	Yield
With selenium; potassium phosphate; copper(l) chloride In dimethyl sulfoxide at 20 - 130℃; for 29h; Inert atmosphere;	84.9%

morpholine (110-91-8) + 3,4-epoxytetrahydrofuran (285-69-8) → trans-3-hydroxy-4-morpholinotetrahydrofuran

Conditions	Yield
at 75 - 80℃; for 3h;	84%

Upstream product

• 1708-29-8 2,5-dihydrofuran 

Downstream Products

• 10295-95-1 4-Pyrrolidino-tetrahydro-furan-3-ol 
• 453-20-3 3-Hydroxytetrahydrofuran 
• 144870-96-2 trans-4-amino-3-hydroxytetrahydrofuran 
• 22554-74-1 (+/-)-trans-tetrahydrofuran-3,4-diol 
• 473-85-8 (3R,4R)-3,4-dihydroxytetrahydrofuran 
• 4358-64-9 cis-1,4-anhydroerythritol 
• 144870-96-2 4-amino-3-hydroxytetrahydrofuran 
• 1178131-96-8 (1S,2S)-4-oxa-2-(4-methoxyphenylamino)cyclopentanol 
• 1178131-96-8 (1R,2R)-4-oxa-2-(4-methoxyphenylamino)cyclopentanol 
• 252332-15-3 N-(3,5-Dichloropyridin-4-yl)-3-(4-hydroxytetrahydrofuran-3-yloxy)-4-methoxybenzamide 

Relevant academic research and scientific papers

A convenient preparation of tetrahydrofuran-based diamines

A convenient, three-step preparation of tetrahydrofuran-based diamines as combinatorial building blocks from 3,4-epoxytetrahydrofuran is described.

SALT FORM AND CRYSTAL FORM OF COMPOUND AS FGFR4 INHIBITOR AND PREPARATION METHOD THEREOF

The present invention provides a salt form, a crystal form, and a preparation method of a compound as an FGFR4 inhibitor and medical uses thereof.

FGFR4 INHIBITOR AND PREPARATION METHOD AND USE THEREOF

Provided are a class of compounds as shown in formula (I) as FGFR4 inhibitors, and pharmaceutically acceptable salts thereof, preparation methods therefor and the use thereof in the preparation of drugs for treating FGFR4-related diseases.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS

The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

Catalytic asymmetric synthesis of thiols

The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected β-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.

Organocatalytic asymmetric hydrolysis of epoxides

The hydrolytic ring opening of epoxides is an important biosynthetic transformation and is also applied industrially. We report the first organocatalytic variant of this reaction, exploiting our recently discovered activation of carboxylic acids with chiral phosphoric acids via heterodimerization. The methodology mimics the enzymatic mechanism, which involves an enzyme-bound carboxylate nucleophile. A newly designed phosphoric acid catalyst displays high stereocontrol in the desymmetrization of meso-epoxides. The methodology shows wide generality with cyclic, acylic, aromatic, and aliphatic substrates. We also apply our method in the first highly enantioselective anti-dihydroxylation of simple olefins.

Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides

The facile synthesis of chiral 1,2-chlorohydrins via the enantioselective ring-opening of meso-epoxides with silicon tetrachloride in the presence of a chiral phosphine oxide was accomplished. The chiral 1,2-chlorohydrins were also obtained from the corresponding cis-alkenes in one-pot without significant loss in the selectivity, thereby permitting easy access to the 1,2-chlorohydrins from cis-alkenes with good yields and enantioselectivities.

SUBSTITUTED CYCLIC COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted cyclic compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

NOVEL TRIAZINE COMPOUNDS

The present invention relates to novel triazine compounds of formula (1), methods of their preparation, pharmaceutical compositions containing these compounds and the use of these compounds to treat proliferative disorders such as tumors and cancers and also other conditions and disorders related to or associated with dysregulation of PI3 Kinases, PI3 Kinase pathway, mTOR and/ or the mTOR pathway.