Product Name

  • Name

    (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE

  • EINECS
  • CAS No. 112837-17-9
  • Article Data10
  • CAS DataBase
  • Density 1.294 g/cm3
  • Solubility
  • Melting Point 39-45 °C
  • Formula C5H6O3
  • Boiling Point 334.8 °C at 760 mmHg
  • Molecular Weight 114.101
  • Flash Point 166.8 °C
  • Transport Information
  • Appearance white to light yellow crystalline powder
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 112837-17-9 ((R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE)
  • Hazard Symbols
  • Synonyms 2(5H)-Furanone,5-(hydroxymethyl)-, (R)-;
  • PSA 46.53000
  • LogP -0.53970

Synthetic route

(Z)-(-)-methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
106757-56-6

(Z)-(-)-methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With camphor-10-sulfonic acid at 25℃; for 3h;97%
With Dowex 50-X2-100 ion-exchange resin In methanol at 20℃; Inert atmosphere;97%
With sulfuric acid In methanol for 1.5h; Ambient temperature;91%
With sulfuric acid In methanol; water for 2h; Ambient temperature;90%
ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate
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

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 2.5h; Inert atmosphere;94%
With sulfuric acid In methanol at 20℃; for 2h; Cyclization;66%
(5R)-phenylseleno-5-methyldihydro-2(3H)-furanone
112775-65-2, 112797-12-3

(5R)-phenylseleno-5-methyldihydro-2(3H)-furanone

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water for 0.5h;83%
C11H12O4S
1403352-72-6

C11H12O4S

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With calcium carbonate In toluene Inert atmosphere; Reflux;80%
(Z)-(R)-4,5-Dihydroxy-pent-2-enoic acid methyl ester

(Z)-(R)-4,5-Dihydroxy-pent-2-enoic acid methyl ester

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With hydrogenchloride In methanol for 12h; Ambient temperature; Yield given;
5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one
116561-10-5

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

A

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

(5S)-5-(hydroxymethyl)-5H-furan-2-one

B

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 16h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(+)-(R)-5-benzyloxymethylfuran-2(5H)-one
85428-26-8

(+)-(R)-5-benzyloxymethylfuran-2(5H)-one

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; for 1h;
5-benzyloxymethyl-3-phenylsulfanyl-dihydrofuran-2-one
364373-27-3

5-benzyloxymethyl-3-phenylsulfanyl-dihydrofuran-2-one

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / NaIO4 / aq. methanol / 20 °C
2: H2 / 10 percent Pd/C / ethyl acetate / 1 h / 20 °C
View Scheme
5-benzyloxymethyl-3-phenylselanyl-dihydrofuran-2-one
364373-24-0

5-benzyloxymethyl-3-phenylselanyl-dihydrofuran-2-one

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / NaIO4 / aq. methanol / 1 h / 20 °C
2: H2 / 10 percent Pd/C / ethyl acetate / 1 h / 20 °C
View Scheme
methyl (R)-4,5-dihydroxy-2-butynoate
174599-52-1

methyl (R)-4,5-dihydroxy-2-butynoate

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Lindlar catalyst / ethyl acetate / 0.42 h / Ambient temperature
2: conc. aq. HCl / methanol / 12 h / Ambient temperature
View Scheme
methyl (R)-4,5-di-O-isopropylidene-4,5-dihydroxy-2-butynoate
174599-51-0

methyl (R)-4,5-di-O-isopropylidene-4,5-dihydroxy-2-butynoate

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90.4 percent / p-TsOH*H2O / methanol / 12 h / Ambient temperature
2: H2 / Lindlar catalyst / ethyl acetate / 0.42 h / Ambient temperature
3: conc. aq. HCl / methanol / 12 h / Ambient temperature
View Scheme
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone
52813-63-5

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / -78 °C
2: 83 percent / 30percent hydrogen peroxide, acetic acid / H2O / 0.5 h
View Scheme
(S)-5-hydroxymethyl-4-phenylsulfanyldihydro-furan-2-one

(S)-5-hydroxymethyl-4-phenylsulfanyldihydro-furan-2-one

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium periodate / methanol; water / 0 °C / Inert atmosphere
2: calcium carbonate / toluene / Inert atmosphere; Reflux
View Scheme
ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate
36326-38-2, 64520-58-7, 91057-97-5, 91926-90-8, 104321-63-3, 124818-64-0, 128525-67-7, 128525-69-9, 104321-62-2

ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere
1.2: 24 h / Inert atmosphere
2.1: sodium periodate / methanol; water / 0 °C / Inert atmosphere
3.1: calcium carbonate / toluene / Inert atmosphere; Reflux
View Scheme
L-5,6-isopropylidene-gulono-1,4-lactone
56710-46-4, 67321-94-2, 69602-93-3, 100227-29-0, 102355-63-5, 121357-95-7, 94697-68-4

L-5,6-isopropylidene-gulono-1,4-lactone

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
1.2: 10 h / 20 °C / Inert atmosphere
2.1: hydrogenchloride / ethanol; water / 2.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
1.2: 10 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere
2.2: 24 h / Inert atmosphere
3.1: sodium periodate / methanol; water / 0 °C / Inert atmosphere
4.1: calcium carbonate / toluene / Inert atmosphere; Reflux
View Scheme
L-gulono-1,4-lactone
1128-23-0

L-gulono-1,4-lactone

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / N,N-dimethyl-formamide / 8 h / 20 °C / pH 3 / Inert atmosphere; Cooling with ice
2.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
2.2: 10 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / ethanol; water / 2.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid / N,N-dimethyl-formamide / 8 h / 20 °C / pH 3 / Inert atmosphere; Cooling with ice
2.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
2.2: 10 h / 20 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere
3.2: 24 h / Inert atmosphere
4.1: sodium periodate / methanol; water / 0 °C / Inert atmosphere
5.1: calcium carbonate / toluene / Inert atmosphere; Reflux
View Scheme
ascorbic acid
50-81-7

ascorbic acid

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: palladium 10% on activated carbon; hydrogen / water / 50 °C / 2585.81 Torr
2.1: sulfuric acid / N,N-dimethyl-formamide / 8 h / 20 °C / pH 3 / Inert atmosphere; Cooling with ice
3.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
3.2: 10 h / 20 °C / Inert atmosphere
4.1: hydrogenchloride / ethanol; water / 2.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: palladium 10% on activated carbon; hydrogen / water / 50 °C / 2585.81 Torr
2.1: sulfuric acid / N,N-dimethyl-formamide / 8 h / 20 °C / pH 3 / Inert atmosphere; Cooling with ice
3.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice
3.2: 10 h / 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere
4.2: 24 h / Inert atmosphere
5.1: sodium periodate / methanol; water / 0 °C / Inert atmosphere
6.1: calcium carbonate / toluene / Inert atmosphere; Reflux
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)-5H-furan-2-one
110171-24-9

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 0.916667h; Inert atmosphere; Cooling with ice;97%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;94%
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere;94%
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one
171595-14-5

(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane 0 deg C, 15 min; rt, 20 min;96%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;92%
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

trityl chloride
76-83-5

trityl chloride

(R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone
101758-68-3

(R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone

Conditions
ConditionsYield
In pyridine; ethanol90%
With pyridine
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

phenylboronic acid
98-80-6

phenylboronic acid

(4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one
950838-18-3

(4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine In 1,4-dioxane; water at 25℃; for 18h; Inert atmosphere; diastereoselective reaction;90%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(4S,5R)-4-(4-fluorophenyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one
950838-19-4

(4S,5R)-4-(4-fluorophenyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Conditions
ConditionsYield
With barium dihydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane; water at 25℃; for 18h; Inert atmosphere; diastereoselective reaction;85%
O-benzyl 2,2,2-trichloroacetimidate
81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(+)-(R)-5-benzyloxymethylfuran-2(5H)-one
85428-26-8

(+)-(R)-5-benzyloxymethylfuran-2(5H)-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 0 - 20℃; for 2.16667h; Addition;84%
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

(5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
85846-73-7

(5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions
ConditionsYield
With silver nitrate In dichloromethane for 48h; Koenigs-Knorr synthesis; Inert atmosphere;29%
diazomethane
186581-53-3, 908094-01-9

diazomethane

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(+)-(R)-umbelactone
69534-86-7

(+)-(R)-umbelactone

Conditions
ConditionsYield
1.) THF/ether; 2.) dioxane, 50 h, reflux; Yield given. Multistep reaction;
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(1S,4R,5R)-4-benzoyloxymethyl-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one
136374-69-1

(1S,4R,5R)-4-benzoyloxymethyl-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one

Conditions
ConditionsYield
Multistep reaction;
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

pivaloyl chloride
3282-30-2

pivaloyl chloride

2,2-Dimethyl-propionic acid (R)-5-oxo-2,5-dihydro-furan-2-ylmethyl ester
130245-25-9

2,2-Dimethyl-propionic acid (R)-5-oxo-2,5-dihydro-furan-2-ylmethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane Ambient temperature; Yield given;
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

ethylenediamine
107-15-3

ethylenediamine

A

7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one

7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one

B

7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one

7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one

Conditions
ConditionsYield
In water 80 deg C, 15 min; RT, 3 h; Yield given. Yields of byproduct given;
...Expand
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

isopropyl alcohol
67-63-0

isopropyl alcohol

(4R,5R)-5-hydroxymethyl-4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one
136265-80-0

(4R,5R)-5-hydroxymethyl-4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one

Conditions
ConditionsYield
for 48h; Irradiation;
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

Cysteamine
60-23-1

Cysteamine

A

(αS,7R)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one

(αS,7R)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one

B

(αS,7S)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one

(αS,7S)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one

Conditions
ConditionsYield
In water 80 deg C, 15 min; RT, 3 h; Yield given. Yields of byproduct given;
...Expand
pyrrolidine
123-75-1

pyrrolidine

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

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

A

(4R,5R)-5-Hydroxymethyl-4-pyrrolidin-1-yl-dihydro-furan-2-one

(4R,5R)-5-Hydroxymethyl-4-pyrrolidin-1-yl-dihydro-furan-2-one

B

5-Hydroxy-1-pyrrolidin-1-yl-pentane-1,4-dione

5-Hydroxy-1-pyrrolidin-1-yl-pentane-1,4-dione

Conditions
ConditionsYield
With chromenone receptor In chloroform-d1 at 20℃; Product distribution; var. chromanone receptors: determination t1/2 and products ratio;
With chromanone receptor In chloroform-d1 at 20℃; Title compound not separated from byproducts;
...Expand
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(2R,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde

(2R,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 94 percent / imidazole / dimethylformamide / 0 - 20 °C
2.1: CuCl; LiCl / tetrahydrofuran / -78 - -50 °C
3.1: DIBAL-H / toluene; diethyl ether / 1 h / -78 °C
4.1: 4.41 g / Ag2O / CH2Cl2 / 48 h / Heating
5.1: O3 / CH2Cl2 / -78 °C
5.2: 83 percent / PPh3 / CH2Cl2 / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
2.1: copper(l) chloride; lithium chloride / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere; Cooling
3.1: diisobutylaluminium hydride / diethyl ether; toluene / 1 h / -78 °C / Inert atmosphere
4.1: silver(l) oxide / dichloromethane / 48 h / Inert atmosphere; Reflux
5.1: ozone / dichloromethane / 0.17 h / -78 °C / Inert atmosphere
5.2: 0 °C / Inert atmosphere
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

tert-butyl (((2R,3S,5S)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane

tert-butyl (((2R,3S,5S)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / imidazole / dimethylformamide / 0 - 20 °C
2: CuCl; LiCl / tetrahydrofuran / -78 - -50 °C
3: DIBAL-H / toluene; diethyl ether / 1 h / -78 °C
4: Ag2O / CH2Cl2 / 48 h / Heating
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

tert-butyl (((2R,3S,5R)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane
909395-03-5

tert-butyl (((2R,3S,5R)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / imidazole / dimethylformamide / 0 - 20 °C
2: CuCl; LiCl / tetrahydrofuran / -78 - -50 °C
3: DIBAL-H / toluene; diethyl ether / 1 h / -78 °C
4: 4.41 g / Ag2O / CH2Cl2 / 48 h / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
2.1: copper(l) chloride; lithium chloride / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere; Cooling
3.1: diisobutylaluminium hydride / diethyl ether; toluene / 1 h / -78 °C / Inert atmosphere
4.1: silver(l) oxide / dichloromethane / 48 h / Inert atmosphere; Reflux
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-vinyl-tetrahydro-furan-2-ol

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-vinyl-tetrahydro-furan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / imidazole / dimethylformamide / 0 - 20 °C
2: CuCl; LiCl / tetrahydrofuran / -78 - -50 °C
3: DIBAL-H / toluene; diethyl ether / 1 h / -78 °C
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(4S,5R)-(-)-5-(tert-butyldiphenylsilanyloxymethyl)-4-vinyldihydrofuran-2-one
160308-93-0

(4S,5R)-(-)-5-(tert-butyldiphenylsilanyloxymethyl)-4-vinyldihydrofuran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / imidazole / dimethylformamide / 0 - 20 °C
2: CuCl; LiCl / tetrahydrofuran / -78 - -50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
2.1: copper(l) chloride; lithium chloride / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere; Cooling
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

(4R,5S)-5-(hydroxymethyl)tetrahydrofuran-2,4-diol
29780-54-9

(4R,5S)-5-(hydroxymethyl)tetrahydrofuran-2,4-diol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 84 percent / trifluoromethanesulfonic acid / CH2Cl2; cyclohexane / 2.17 h / 0 - 20 °C
2.1: Li / tetrahydrofuran / 0 °C / sonication
2.2: CuCN / tetrahydrofuran / 0.5 h / -45 °C
2.3: 90 percent / tetrahydrofuran / 1 h / -45 °C
3.1: 65 percent / AcOOH/AcOH; Br2 / 5 h / 20 °C
4.1: 60 percent / 2-methyl-2-butene; BH3 / tetrahydrofuran / 24 h / 20 °C
5.1: 80 percent / formic acid / 10 percent Pd/C / methanol / 1 h / 20 °C
View Scheme
(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one
112837-17-9

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one

α,β-(4R,5S)-(-)-5-benzyloxymethyltetrahydrofuran-2,4-diol

α,β-(4R,5S)-(-)-5-benzyloxymethyltetrahydrofuran-2,4-diol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 84 percent / trifluoromethanesulfonic acid / CH2Cl2; cyclohexane / 2.17 h / 0 - 20 °C
2.1: Li / tetrahydrofuran / 0 °C / sonication
2.2: CuCN / tetrahydrofuran / 0.5 h / -45 °C
2.3: 90 percent / tetrahydrofuran / 1 h / -45 °C
3.1: 65 percent / AcOOH/AcOH; Br2 / 5 h / 20 °C
4.1: 60 percent / 2-methyl-2-butene; BH3 / tetrahydrofuran / 24 h / 20 °C
View Scheme

2(5H)-Furanone,5-(hydroxymethyl)-, (5R)- Specification

This chemical is called 2(5H)-Furanone,5-(hydroxymethyl)-, (5R)-, and its IUPAC name is (2R)-2-(hydroxymethyl)-2H-furan-5-one With the molecular formula of C5H6O3, its molecular weight is 114.1. The CAS registry number of this chemical is 112837-17-9. Additionally, its product categories are Pharmacetical; Chiral Building Blocks; Furans; Heterocyclic Building Blocks.

Other characteristics of the can be summarised as followings: (1)ACD/LogP: -1.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.81; (4)ACD/LogD (pH 7.4): -1.81; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.47; (8)ACD/KOC (pH 7.4): 2.47; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.502; (14)Molar Refractivity: 26.01 cm3; (15)Molar Volume: 88.1 cm3; (16)Polarizability: 10.31×10-24cm3; (17)Surface Tension: 45.3 dyne/cm; (18)Density: 1.294 g/cm3; (19)Flash Point: 166.8 °C; (20)Enthalpy of Vaporization: 66.94 kJ/mol; (21)Boiling Point: 334.8 °C at 760 mmHg; (22)Vapour Pressure: 8.79E-06 mmHg at 25°C. 

You can still convert the following datas into 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-/m1/s1
3.InChIKey: AWNLUIGMHSSXHB-SCSAIBSYBD

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