112837-17-9

Basic information

• Product Name: (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE
• Synonyms: (R)-5-HYDROXYMETHYL-5H-FURAN-2-ONE;(R)-(-)-5-HYDROXYMETHYL-2(5H)-FURANONE;(R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE;RARECHEM AK HZ 0033;(R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE 98%;(R)-(+)-5-(Hydroxymethyl)-2(5H)-furanone,98%;(R)-5-(Hydroxymethyl)furan-2(5H)-one
• CAS NO: 112837-17-9
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.1
• Product Categories: pharmacetical;Chiral Building Blocks;Furans;Heterocyclic Building Blocks
• Mol File: 112837-17-9.mol

Chemical Properties

• Melting Point: 39-45 °C
• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 166.8 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.294 g/cm³
• PKA: 13.51±0.10(Predicted)
• CAS DataBase Reference: (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE(112837-17-9)
• EPA Substance Registry System: (R)-(+)-5-(HYDROXYMETHYL)-2(5H)-FURANONE(112837-17-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 112837-17-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

Synthetic route

(Z)-(-)-methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (106757-56-6) → (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

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

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

Conditions	Yield
With dihydrogen peroxide; acetic acid In water for 0.5h;	83%

C11H12O4S (1403352-72-6) → (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

Conditions	Yield
With calcium carbonate In toluene Inert atmosphere; Reflux;	80%

(Z)-(R)-4,5-Dihydroxy-pent-2-enoic acid methyl ester → (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

Conditions	Yield
With hydrogenchloride In methanol for 12h; Ambient temperature; Yield given;

5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one (116561-10-5) → (5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) + (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

Conditions	Yield
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-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; for 1h;

5-benzyloxymethyl-3-phenylsulfanyl-dihydrofuran-2-one (364373-27-3) → (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9)

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

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

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

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

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

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

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

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

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

Conditions	Yield
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) + tert-butylchlorodiphenylsilane (58479-61-1) → (R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)-5H-furan-2-one (110171-24-9)

Conditions	Yield
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) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one (171595-14-5)

Conditions	Yield
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) + trityl chloride (76-83-5) → (R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone (101758-68-3)

Conditions	Yield
In pyridine; ethanol	90%
With pyridine

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + phenylboronic acid (98-80-6) → (4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one (950838-18-3)

Conditions	Yield
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) + (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (4S,5R)-4-(4-fluorophenyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (950838-19-4)

Conditions	Yield
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) + (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (+)-(R)-5-benzyloxymethylfuran-2(5H)-one (85428-26-8)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 0 - 20℃; for 2.16667h; Addition;	84%

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (5'-oxo-2',5'-dihydrofuran-2'-yl)methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (85846-73-7)

Conditions	Yield
With silver nitrate In dichloromethane for 48h; Koenigs-Knorr synthesis; Inert atmosphere;	29%

diazomethane (186581-53-3, 908094-01-9) + (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (+)-(R)-umbelactone (69534-86-7)

Conditions	Yield
1.) THF/ether; 2.) dioxane, 50 h, reflux; Yield given. Multistep reaction;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (1S,4R,5R)-4-benzoyloxymethyl-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one (136374-69-1)

Conditions	Yield
Multistep reaction;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (R)-5-oxo-2,5-dihydro-furan-2-ylmethyl ester (130245-25-9)

Conditions	Yield
With pyridine In dichloromethane Ambient temperature; Yield given;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + ethylenediamine (107-15-3) → 7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one + 7-(1,2-dihydroxyethyl)-<1,4>-diazepan-5-one

Conditions	Yield
In water 80 deg C, 15 min; RT, 3 h; Yield given. Yields of byproduct given;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + isopropyl alcohol (67-63-0) → (4R,5R)-5-hydroxymethyl-4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one (136265-80-0)

Conditions	Yield
for 48h; Irradiation;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) + Cysteamine (60-23-1) → (αS,7R)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one + (αS,7S)-7-(1,2-dihydroxyethyl)-<1,4>-thiazepan-5-one

Conditions	Yield
In water 80 deg C, 15 min; RT, 3 h; Yield given. Yields of byproduct given;

pyrrolidine (123-75-1) + (R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (4R,5R)-5-Hydroxymethyl-4-pyrrolidin-1-yl-dihydro-furan-2-one + 5-Hydroxy-1-pyrrolidin-1-yl-pentane-1,4-dione

Conditions	Yield
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;

(R)-(+)-5-(hydroxymethyl)furan-2(5H)-one (112837-17-9) → (2R,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde

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

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

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

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

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

Conditions

Yield

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

Conditions	Yield
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

Upstream product

• 112775-65-2 (5R)-phenylseleno-5-methyldihydro-2(3H)-furanone 
• 116561-10-5 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one 
• 36326-38-2 ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate 
• 85428-26-8 (+)-(R)-5-benzyloxymethylfuran-2(5H)-one 
• 364373-24-0 5-benzyloxymethyl-3-phenylselanyl-dihydrofuran-2-one 
• 174599-51-0 methyl (R)-4,5-di-O-isopropylidene-4,5-dihydroxy-2-butynoate 
• 1403352-72-6 C₁₁H₁₂O₄S 
• 1128-23-0 L-gulono-1,4-lactone 
• 50-81-7 ascorbic acid 
• 56710-46-4 L-5,6-isopropylidene-gulono-1,4-lactone 
• 36326-38-2 ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 174599-52-1 methyl (R)-4,5-dihydroxy-2-butynoate 
• 364373-27-3 5-benzyloxymethyl-3-phenylsulfanyl-dihydrofuran-2-one 

Downstream Products

• 136374-69-1 (1S,4R,5R)-4-benzoyloxymethyl-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one 
• 101758-68-3 (R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone 
• 110171-24-9 (R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one 
• 85428-26-8 (+)-(R)-5-benzyloxymethylfuran-2(5H)-one 
• 909395-03-5 tert-butyl (((2R,3S,5R)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane 
• 160308-93-0 (4S,5R)-(-)-5-(tert-butyldiphenylsilanyloxymethyl)-4-vinyldihydrofuran-2-one 
• 289660-11-3 (4R,5S)-(-)-5-benzyloxymethyl-4-hydroxy-dihydro-furan-2-one 
• 289660-10-2 (4R,5S)-(-)-5-benzyloxymethyl-4-(dimethylphenylsilanyl)dihydrofuran-2-one 
• 202392-40-3 3-[(2R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-tetrahydro-furan-2-yl]-propan-1-ol 
• 202392-41-4 tert-Butyl-[(2R,3R,5R)-5-(3-methoxymethoxy-propyl)-3-methyl-tetrahydro-furan-2-ylmethoxy]-diphenyl-silane 
• 110098-09-4 (4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-dihydro-furan-2-one 
• 202392-39-0 ((2R,3R,5R)-5-Allyl-3-methyl-tetrahydro-furan-2-ylmethoxy)-tert-butyl-diphenyl-silane 
• 1026246-65-0 (2R,3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethyl-2-(3-oxo-2-trimethylsilanyl-butyl)-cyclohexanone 
• 188120-39-0 (2R,3R,4S)-4-tert-butyldimethylsilyloxy-2,3-dimethylcyclohexanone 

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Total synthesis of branimycin: An evolutionary approach

The first total synthesis of the macrolactone antibiotic branimycin (4) has been described. The key disconnection leads to a cis-dehydrodecalone core and a polyketide side chain which are connected via organometallic addition. The dehydrodecalone core was targeted via altogether five different approaches featuring various kinds of chiral elements and ring-closing methodology. In the end the most successful method starting from diepoxynaphthalene 109 was chosen to carry on with the synthesis. Thus the oxygen functions and carbon appendages were introduced via organometallic desymmetrization reactions to generate epoxy ketone 107, to which vinyl iodide 11 was added after conversion into the organolithium species. The synthesis was completed by introducing the ester side chain via Michael addition and subsequent macrolactonization. Competitive approach: The first total synthesis of the macrolactone antibiotic branimycin is described (see figure). The dehydrodecalin core was targeted via five competing approaches featuring various kinds of chiral elements and ring-closing methodology. In this "Darwinian" struggle the most successful route emerged and led to the completion of the synthesis. Copyright

A pyrrolysine analogue for protein click chemistry

(Chemical Equation Presented) Ignoring the STOP sign: A pyrrolysine analogue bearing a terminal alkyne was site-specifically incorporated into recombinant calmodulin (CaM) through a UAG codon. The resulting protein was labeled with an azide-containing dye using a copper(I)-catalyzed click reaction. Subsequent application of an orthogonal cysteine tagging method yielded a CaM labeled with two distinct fluorophores that enabled its study by FRET spectroscopy.

Convenient new syntheses of R-(+)-5-benzyloxymethyl-5H-furan-2-one- a building block en route to L-nucleosides

R-(+)-5-Benzyloxymethyl-5H-furan-2-one (R-(1)) was obtained from commercially available R-(-)-2-benzyloxymethyl oxirane (R-(2)) in two and three steps, respectively. Key steps are a) the nucleophilic ring opening of the oxirane moiety with dianions derived from either PhSeCH2CO2H or PhSCH2CO2H; b) oxidation to the corresponding 1-oxides and c) concomitant or thermally induced syn-elimination. R-(1) was obtained with ≥97% ee and ≥95% ee, respectively.

A novel synthesis of 2-deoxy-L-ribose

We report a new synthesis of 2-deoxy-L-ribose starting from the commercially available (R)-(+)-5-hydroxymethyl-5H-furan-2-one. The key step is a 1,4-addition of (PhMe2Si)2Cu(CN)Li2 which proceeds with complete diastereoselection. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis of Optically Active Butenolides and γ-Lactones by the Sharpless Asymmetric Dihydroxylation of β,γ-Unsaturated Carboxylic Esters

Keywords: asymmetric synthesis; butenolides; dihydroxylations; furanones; lactones

Synthetic study on gymnodimine: Highly stereoselective construction of substituted tetrahydrofuran and cyclohexene moieties

The synthetic studies on gymnodimine, a shellfish toxin, are described. This marine toxin consists of 16-membered carbocycle, tetrahydrofuran, and spiro-imine moieties. Our synthetic strategy involves the stereoselective allylation of tetrahydrofuran compound and the exo-selective intramolecular Diels-Alder reaction.

Synthesis of novel L-series 2',3'-dideoxy-3'-hydroxy-methyl-nucleosides and a convenient method for the separation of nucleoside anomers

Photoinduced addition of methanol to 5(R)-(tert- butyldimethylsilyloxymethyl) -2(5H)-furan-2-one (derived from L-gulono-1,4- lactone) provided the photoadduct 5(R)-(tert-butyldimethylsiloxymethyl)- 4(S)-hydroxymethyl-tetrahydrofuran-2-one, which was converted into two L- series-2',3'-dideoxy-3'-hydroxymethyl-nucleosides. In addition, we describe a new method for the chromatographic separation of cytidine anomers using a N- 2-(4-nitrophenyl)ethyl carbamate derivative.

Lipase-mediated preparation of optically pure four-carbon di- and triols from a meso-precursor

An expedient route to optically pure four-carbon di- and triols, prepared from a meso-symmetric four-carbon precursor by employing lipase-mediated kinetic resolution as a key step.

SYNTHESIS OF THE ENANTIOMERS OF UMBELACTONE. CONFIGURATIONAL ASSIGNMENT OF THE NATURAL PRODUCT.

Both (+)- and (-)-umbelactone have been synthetized from (R)-γ-hydroxymethyl-γ-butyrolactone and D-ribonolactone, respectively.The absolute configuration of the natural product has shown to be R-(+).