(S)-(-)-5-Hydroxymethyl-2(5H)-furanone supplier

Name
(S)-(-)HYDROXYMETHYL-3(2H)-FURANONE
EINECS
CAS No. 78508-96-0
Article Data46
CAS DataBase
Density 1.295 g/cm³
Solubility Slightly soluble in water.
Melting Point 41-43 °C(lit.)
Formula C₅H₆O₃
Boiling Point 334.754 °C at 760 mmHg
Molecular Weight 114.101
Flash Point 166.808 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2(5H)-Furanone,5-(hydroxymethyl)-, (S)-;(5S)-Hydroxymethyl-5H-furan-2-one;(S)-(-)-5-(Hydroxymethyl)-2(5H)furanone;(S)-5-(Hydroxymethyl)furan-2(5H)-one;(S)-5-Hydroxy-2-penten-4-olide;l-Ranunculin aglycon;
PSA 46.53000
LogP -0.53970

Synthetic route

: 81703-94-8
methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With sulfuric acid In methanol at 23℃; for 2h;	97%
With camphor-10-sulfonic acid In methanol at 20℃;	95%
With sulfuric acid In methanol at 20℃; for 2h;	93%
With hydrogenchloride In water; acetonitrile for 2.75h; Product distribution; Further Variations:; Reagents;	84%
With camphor-10-sulfonic acid at 25℃; for 3h;

: 36326-38-2, 64520-58-7, 91057-97-5, 91926-90-8, 104321-62-2, 124818-64-0, 128525-67-7, 128525-69-9, 104321-63-3
ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With sulfuric acid In methanol for 0.5h; Ambient temperature;	95%
With sulfuric acid In methanol

: 91926-90-8
ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With hydrogenchloride	90%
With hydrogenchloride In ethanol for 2h; Ambient temperature;	81%
With sulfuric acid

: 76236-32-3
2,3-dideoxy-5-O-(triphenylmethyl)-D-glycero-pent-2-enono-1,4-lactone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Ambient temperature;	90%
With hydrogenchloride; methanol

: 66601-82-9
methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With sulfuric acid In methanol at 25℃; for 1h;	90%
With sulfuric acid; water In methanol at 20℃; for 2h; Cyclization;	85%

: 37112-31-5
levoglucosenone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 50℃; for 10h; Baeyer-Villiger Ketone Oxidation; Inert atmosphere; Cooling with ice;	84%
Stage #1: levoglucosenone With Candida antarctica B lipase; dihydrogen peroxide In ethyl acetate at 40℃; for 8h; Baeyer-Villiger Ketone Oxidation; Green chemistry; Enzymatic reaction; Stage #2: In 1,4-dioxane at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Green chemistry; regioselective reaction;	83%
With dihydrogen peroxide In water at 0 - 50℃; for 1h; Baeyer-Villiger Ketone Oxidation;	76%

: 105122-15-4
(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With water; acetic acid In tetrahydrofuran at 24℃; for 22h;	82%
With acetic acid In tetrahydrofuran; water at 24℃; for 22h;	82%

: 37112-31-5
levoglucosenone

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 85846-84-0
(-)-(S)-5-formyloxymethyloxol-3-en-2one

Conditions

Conditions	Yield
With dihydrogen peroxide In water at 50℃; for 10h; Baeyer-Villiger Ketone Oxidation; Inert atmosphere; Cooling with ice; Large scale;	A 71% B n/a
With peracetic acid; dimethylsulfide; acetic acid 1.) RT, 2 d, 2.) 1 h; Multistep reaction. Title compound not separated from byproducts;
With Candida antarctica B lipase; dihydrogen peroxide In ethyl acetate at 40℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Baeyer-Villiger Ketone Oxidation; Green chemistry; Enzymatic reaction; regioselective reaction;

: 5336-08-3
D-Ribono-1,4-lactone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With methyltrioxorhenium(VII) at 170 - 180℃; for 15h; Sealed tube; Inert atmosphere;	70%
Multi-step reaction with 2 steps 1: 1.) THF, 12 h, reflux, 2.) 7 d 2: 68 percent / 220 °C / 40 Torr View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 12 h / Heating 2: 68 percent / 220 °C / 40 Torr View Scheme
With methyltrioxorhenium(VII) at 155℃; for 2h; Inert atmosphere;	23.5 mg

: 78508-93-7
2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
at 220℃; under 40 Torr;	68%

: 78508-93-7
(+)-2,3-O-ethoxymethylene-D-ribonolactone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
at 220℃; under 40 Torr;	68%

: 2-deoxy-3,5-di-O-(p-chlorobenzoyl)-γ-D-ribonolactone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h;	65%

: 66601-82-9
methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 64520-58-7
ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Conditions

Conditions	Yield
With sulfuric acid In methanol for 0.5h; Ambient temperature;	A 63% B n/a

: (S)-tert-butyl trans-4,5-dihydroxylpent-2-enoate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With phenanthrene In dichloromethane at 25 - 30℃; UV-irradiation;	61%

: 36326-38-2
3-<(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>prop-2-enoic acid ethyl ester

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 81703-93-7
methyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

Conditions

Conditions	Yield
With sulfuric acid In methanol for 0.5h; Ambient temperature;	A 60% B n/a

: (S)-tert-butyl trans-4,5-dihydroxylpent-2-enoate

A: 1239346-69-0
tert-butyl 5-hydroxy-4-oxopentanoate

B: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With adenosine In dichloromethane at 25 - 30℃; UV-irradiation;	A 51% B n/a

: 37112-31-5
levoglucosenone

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 82540-80-5
2-deoxy-3-O-methyl-D-erythro-pentono-1,4-lactone

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In methanol at 18℃; for 408h;	A 13% B 4%

: 85846-83-9
(-)-(S)-5-acetyloxymethyl-2(5H)-furanone

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 5℃; for 18h; Yield given;

: 81668-95-3
tert-butyl 6-O-acetyl-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With peracetic acid for 12h;

: 78138-89-3
2-Bromo-2-deoxy-D-arabinono-γ-lactone

A: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

B: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr;

: 105866-01-1, 105866-02-2, 115731-00-5
(3R/S,4S)-5-Hydroxy-4-phenylsulfinyl-4-pentanolide

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With calcium carbonate In toluene for 3h; Heating; Yield given;

: 122-51-0
orthoformic acid triethyl ester

: 5336-08-3
D-Ribono-1,4-lactone

A: 108-28-1
protoanemonin

B: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
1.) THF, reflux; 2.) 220 deg C, 18 Hgmm; Multistep reaction;

...Expand

: 5336-08-3
D-Ribono-1,4-lactone

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 85694-09-3
(S)-(-)-γ-bromometil-α,β-butenolide

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 4753-03-1
1-(2-deoxy-2-iodo-β-D-ribofuranosyl)uracil

A: 3736-77-4
2,2'-Anhydrouridine

B: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

C: 3'-keto-2'-deoxyuridine

D: 1-((2R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

E: 2'β-iodo-2'-deoxyuridine

F: 34371-14-7
2-deoxy-D-ribonolactone

Conditions

Conditions	Yield
In water-d2 for 4h; Product distribution; Mechanism; Irradiation; var. solvents, in the presence of O2, also <1'-D>-2'α-iodo-2'-deoxyuridine, other deoxyoligonucleotides;	A 2.0 % Spectr. B 2.0 % Spectr. C 1.0 % Spectr. D 4.0 % Spectr. E 13 % Spectr. F 1.0 % Spectr.

...Expand

: 116561-10-5
5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one

A: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

B: 112837-17-9
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 16h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 106183-54-4, 106183-55-5
tert-butyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / CH3COOH / tetrahydrofuran; H2O / 22 h / 24 °C View Scheme
Multi-step reaction with 3 steps 1: 50 percent aq. CF3COOH / 2 h / 90 - 95 °C 2: 1.)t-BuMe2SiCl; 2.) SOCl2, pyridine / 1.) CH2Cl2, 20 deg C., 16h; 2.) CH2Cl2, 24 deg C, 22h 3: 82 percent / H2O, AcOH / tetrahydrofuran / 22 h / 24 °C View Scheme

: 79060-23-4
(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / Et3N / CH2Cl2 / 1 h / 20 °C 2: 84 percent / HCl / H2O; acetonitrile / 2.75 h View Scheme

: 79698-71-8
tert-butyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / methanol / 1 h 2: pyridine, dimethylaminopyridine / CH2Cl2 / 1 h 3: 40percent aq. AcOOH / 12 h View Scheme

: 119794-56-8
tert-butyl 3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine, dimethylaminopyridine / CH2Cl2 / 1 h 2: 40percent aq. AcOOH / 12 h View Scheme

: 3366-47-0
2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / BF3*Et2O / CH2Cl2 / 72 h 2: K2CO3 / methanol / 1 h 3: pyridine, dimethylaminopyridine / CH2Cl2 / 1 h 4: 40percent aq. AcOOH / 12 h View Scheme

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105122-15-4
(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 1h;	100%
With 1H-imidazole In dichloromethane at 0 - 23℃; for 1h;	99%
With 1H-imidazole In dichloromethane at 20℃; for 3h;	98%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 112-64-1
tetradecanoyl chloride

: 138433-97-3
5-O-tetradecanoyl-2,3-didehydro-2,3-dideoxy-D-glycero-pentono-1,4-lactone

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane for 24h; Ambient temperature;	97%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 0℃; for 0.75h;	97%
With ammonium nitrate In N,N-dimethyl-formamide at 0 - 25℃; for 12.5h;	95%
With dmap	94%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 101244-99-9
(+/-)-3-tert-butyldimethylsilyloxy-1-cyclopentane-1-carboxylic acid

: 101244-80-8, 101244-81-9
(-)-R-4-(3-tert-butyldimethylsilyloxycyclopent-1-ene-1-carbonyloxymethyl)but-2-en-4-olide

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane	96%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	96%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 4h; Ambient temperature;	96%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃;	90%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃;	86%

: 110-87-2
3,4-dihydro-2H-pyran

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 128387-70-2
(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In tetrahydrofuran at 10℃; for 15h;	95%
With camphor-10-sulfonic acid	93%
With toluene-4-sulfonic acid In dichloromethane at 23℃; for 8h;	78%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 8h;	78%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 3282-30-2
pivaloyl chloride

: 139230-94-7
(-)-(S)-5-pivaloyloxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 24h; Esterification;	95%
With pyridine; dmap In dichloromethane for 29h; Ambient temperature;	89%
With pyridine In dichloromethane at 23℃; for 12h;	81%
With pyridine In dichloromethane at 0 - 20℃;	81%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 542-92-7
cyclopenta-1,3-diene

: (2R,5S,6S)-5-Hydroxymethyl-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

Conditions

Conditions	Yield
With zinc(II) iodide In dichloromethane at 15℃; for 21h;	95%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 67-63-0
isopropyl alcohol

: 136265-74-2
(4S,5S)-5-hydroxymethyl-4-C-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one

Conditions

Conditions	Yield
for 48h; Irradiation;	94%
With acetophenone for 18h; Irradiation;

: 14602-86-9
(1R,2S,5R)-menthyl chloroformate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 386744-36-1
(1R,2S,5R)-menthyl [(5S)-2-oxo-2,5-dihydrofuran-5-yl]methyl carbonate

Conditions

Conditions	Yield
With pyridine In dichloromethane Cooling;	93%

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 72605-53-9
γ-benzyloxymethyl-α,β-butenolide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 4h; Inert atmosphere;	93%
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 0℃; for 4h; Inert atmosphere;

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 252667-55-3
(S)-5-(4,4'-dimethoxytrityloxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With pyridine for 3h;	92%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 75-36-5
acetyl chloride

: 85846-83-9
(-)-(S)-5-acetyloxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	92%
With pyridine In dichloromethane at 0℃; for 1h;	92%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 407-25-0
trifluoroacetic anhydride

: 139230-95-8
(-)-(S)-5-trifluoroacetyloxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
for 6h;	91%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 98-88-4
benzoyl chloride

: 96086-02-1
(5S)-5-(benzoyloxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	86%
With pyridine In dichloromethane at 0℃; for 1h;	86%
With pyridine In dichloromethane at 0℃; for 1h;	85%

: 4-tert-butoxy-3,4-dihydro-2H-pyrrole 1-oxide

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 8-tert-butoxy-3-hydroxymethyl-hexahydro-furo[3,4-d]pyrrolo[1,2-b]isoxazol-1-one

Conditions

Conditions	Yield
In toluene Heating;	86%

: 13154-24-0
triisopropylsilyl chloride

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 848413-91-2
(S)-(5-O-triisopropylsilanyloxymethyl)furan-2(5H)-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 18h;	86%
Stage #1: (5S)-5-(hydroxymethyl)-5H-furan-2-one With 1H-imidazole In dichloromethane Stage #2: triisopropylsilyl chloride In dichloromethane at 25℃;	65%

: 6485-79-6
chlorotriisopropylsilane

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 848413-91-2
(S)-(5-O-triisopropylsilanyloxymethyl)furan-2(5H)-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 18h;	86%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 108-24-7
acetic anhydride

: 85846-83-9
(-)-(S)-5-acetyloxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 24h;	83%
With pyridine In dichloromethane for 14h; Ambient temperature;	79%
With pyridine; dmap In dichloromethane for 1.5h; Yield given;

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 76-83-5
trityl chloride

: 76236-32-3
2,3-dideoxy-5-O-(triphenylmethyl)-D-glycero-pent-2-enono-1,4-lactone

Conditions

Conditions	Yield
With pyridine at 70℃; for 16h; tritylation;	83%
In pyridine	65%
With pyridine 1.) 20 min, 2.) 72 h, room tempreature;	64.7%
With pyridine In dichloromethane for 4h; Ambient temperature;	50%
With pyridine In dichloromethane at 0℃; for 24h;	40%

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 2094-72-6
1-Adamantanecarbonyl chloride

: 1071533-93-1
(-)-(S)-5-adamantanecarbonyloxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃;	83%

: 1560-11-8
cyclopent-1-enecarboxylic acid

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 162086-61-5
(-)-R-4-(cyclopent-1-ene-1-carbonyloxymethyl)but-2-en-4-olide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;	82%

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: (S)-5-(2-methoxyethoxy)methoxymethyl-2(5H)-furanone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	82%

(S)-(-)-5-Hydroxymethyl-2(5H)-furanone Specification

The (S)-(-)-5-Hydroxymethyl-2(5H)-furanone, with the CAS registry number 78508-96-0, has the systematic name of (5S)-5-(hydroxymethyl)furan-2(5H)-one. It belongs to the following product categories: Chiral Reagent; Chiral Building Blocks; Furans; Heterocyclic Building Blocks. And the molecular formula of the chemical is C₅H₆O₃. What's more, while dealing with this chemical, you should avoid contact with skin and eyes.

The characteristics of (S)-(-)-5-Hydroxymethyl-2(5H)-furanone are as followings: (1)ACD/LogP: -1.92; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 46.53 Å²; (7)Index of Refraction: 1.502; (8)Molar Refractivity: 26.015 cm³; (9)Molar Volume: 88.121 cm³; (10)Polarizability: 10.313×10^-24cm³; (11)Surface Tension: 45.369 dyne/cm; (12)Density: 1.295 g/cm³; (13)Flash Point: 166.808 °C; (14)Enthalpy of Vaporization: 66.937 kJ/mol; (15)Boiling Point: 334.754 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C\1O[C@@H](/C=C/1)CO
(2)InChI: InChI=1/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1
(3)InChIKey: AWNLUIGMHSSXHB-BYPYZUCNBO

Product Name

(S)-(-)HYDROXYMETHYL-3(2H)-FURANONE

Synthetic route

(S)-(-)-5-Hydroxymethyl-2(5H)-furanone Specification

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