599-04-2

Basic information

• Product Name: D-(-)-PANTOLACTONE
• Synonyms: (R)-(-)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(R)-DIHYDRO-3-HYDROXY-4,4-DIMETHYL-2(3H)-FURANONE;(R)-(-)-BETA,BETA-DIMETHYL-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE;(R)-(-)-PANTOLACTONE;(R)-(-)-ALPHA-HYDROXY-BETA,BETA-DIMETHYL-GAMMA-BUTYROLACTONE;R(-)-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE;R(-)-2-HYDROXY-3,3-DIMETHYL-GAMMA-BUTYROLACTONE;PANTOIC ACID GAMMA-LACTONE
• CAS NO: 599-04-2
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• EINECS: 209-963-3
• Product Categories: Pharmaceutical Intermediates;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 599-04-2.mol
• Article Data: 130

Chemical Properties

• Melting Point: 91 °C(lit.)
• Boiling Point: 120-122 °C15 mm Hg(lit.)
• Flash Point: 120-122°C/15mm
• Appearance: White/Crystals or Crystalline Powder
• Density: 1.1066 (rough estimate)
• Vapor Pressure: 0.0181mmHg at 25°C
• Refractive Index: -50.8 ° (C=2, H2O)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly), Water (S
• PKA: 13.12±0.40(Predicted)
• Water Solubility: almost transparency
• Sensitive: Hygroscopic
• Merck: 14,7013
• BRN: 80957
• CAS DataBase Reference: D-(-)-PANTOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-PANTOLACTONE(599-04-2)
• EPA Substance Registry System: D-(-)-PANTOLACTONE(599-04-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 1
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 599-04-2(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER OR CRYSTALS

Uses

Different sources of media describe the Uses of 599-04-2 differently. You can refer to the following data:
1. D-(-)-PANTOLACTONE is an important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia.
2. D-(-)-Pantolactone is a chiral auxiliary used in many asymmetric synthesis reactions.It can be used as a chiral starting material to synthesize:An insect sex pheromone named 1S,2S,3R-1-acetoxymethyl-2,3,4,4-tetrameth-ylcyclopentane.(-)-Enantiomer of (R)-8-hydroxy-4,7,7-trimethyl-7,8-dihydrocyclopenta[e]isoindole-1,3(2H,6H)-dione, a norsesquiterpene alkaloid.A bicyclic diterpene named isofregenedadiol.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Purification Methods

Recrystallise the lactone from Et2O/pet ether, diisopropyl ether or *C6H6/pet ether and sublime it at 25o/0.0001mm. It hydrolyses readily to the hydroxy-acid and racemises when heated above 145o. The Brucine salt has m 211-212o (from EtOH). [Kuhn & Wieland Chem Ber 73 1134 1940, and Stiller et al. J Am Chem Soc 62 1779 1940, Bental & Tishler J Am Chem Soc 68 1463 1946, Beilstein 18/1 V 22.]

InChI:InChI=1/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3

Synthetic route

ketopantolactone (13031-04-4) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With chiral Rh complex derived from N,O-bis(dicyclopentylphosphinyl)-(S)-2-hydroxymethylindoline; hydrogen In toluene at 20℃; under 750.06 Torr; for 0.17h;	100%
With (R)-N-dicyclohexylphosphino-N-methyl-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine; hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate In ethyl acetate at 25℃; under 15514.4 Torr; for 1.25h;	99%
With D-glucose; Rhodotorula minuta IFO 0920 at 28℃; for 36h;	80.3%

D-potassium pantoate → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 0.5h; pH=1 - 2; Reagent/catalyst;	96.9%

(R)-2,4-dihydroxy-N-<(1R)-2-endo-hydroxy-3-endo-bornyl>-3,3-dimethylbutyramide (107730-03-0) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 40℃; for 1h;	96.8%

ketopantolactone (13031-04-4) → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine In toluene at 50℃; under 37503 Torr; for 45h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 95%
With hydrogen; (S)-Cp-isoAlaNOP - 2 In toluene at 20℃; under 760 Torr; for 0.5h; Title compound not separated from byproducts;
With magnesium(II) perchlorate; (S)-3-(N,N-dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine In [D3]acetonitrile -25 degC to r.t, 1 h;

D-sodium pantoate (60979-68-2) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 0.5h; pH=1 - 2; Reagent/catalyst;	94.7%

3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one (133094-78-7) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With phosphomolybdic acid hydrate; silica gel In tetrahydrofuran at 20℃; for 12h;	94%
With iron(III) p-toluenesulfonate hexahydrate In methanol for 27.5833h; Reflux; chemoselective reaction;	84%

(R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on (20374-33-8) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol optical yield given as %ee;	93%

2(R)-hydroxy-3,3-dimethyl-4-oxo-butxyric acid ethyl ester (1196498-52-8) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃;	93%
With sodium cyanoborohydride In methanol Reagent/catalyst; Solvent; Cooling with ice;	93%
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / diethyl ether / 20 °C 1.2: Saturated solution 2.1: toluene-4-sulfonic acid / diethyl ether / 20 °C View Scheme
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; (R)-N-(2-hydroxyethyl)pyrrolidine-2-carboxamide; sodium formate In water; tert-butyl alcohol at 40℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere;

(R)-4-Chloro-2-hydroxy-3,3-dimethyl-butyronitrile → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h;	88%

methyl 2-hydroxy-3,3-dimethyl-4-oxobutanoate → (R)-Pantolacton (599-04-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol Cooling with ice;	87%

D-pantoic acid (1112-33-0) → (R)-Pantolacton (599-04-2)

Conditions	Yield
at 90 - 95℃;	85%

(R)-2-Hydroxy-4-methoxy-3,3-dimethyl-butyronitrile → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h;	78%

(R)-acetic acid 4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl ester (28227-36-3) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With sodium methylate In methanol for 0.5h; Ambient temperature;	76.6%

(R)-4-Bromo-2-hydroxy-3,3-dimethyl-butyronitrile → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h;	65%

(R)-2,4-Dihydroxy-3,3-dimethylbutyronitrile (134929-92-3) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride for 8.5h; Ambient temperature;	62%
With hydrogenchloride In methanol; water at 20℃; Reflux;

(R)-4-Allyloxy-2-hydroxy-3,3-dimethyl-butyronitrile → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h;	62%

(R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyric acid (158045-18-2) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform	60%

methanol (67-56-1) + C13H18O6 (861855-32-5) → C8H12O4 (861855-40-5) + methyl-2,3-dideoxy-4,6-O-methylene-D-erythro-hex-2-enopyranoside + (R)-Pantolacton (599-04-2)

Conditions	Yield
lanthanum(lll) triflate In acetonitrile at 20℃; for 15h; Product distribution / selectivity;	A n/a B n/a C 60%
erbium(III) triflate In acetonitrile Product distribution / selectivity;
scandium tris(trifluoromethanesulfonate) In acetonitrile Product distribution / selectivity;
iron(III) chloride In acetonitrile Product distribution / selectivity;

(R)-4-Ethoxy-2-hydroxy-3,3-dimethyl-butyronitrile → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h;	55%

methanol (67-56-1) + C13H18O6 (861855-32-5) → methyl-2,3-dideoxy-4,6-O-methylene-D-erythro-hex-2-enopyranoside + C9H16O5 (1222471-59-1) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With 10M acid-treated K10 Montmorillonite at 40℃; for 8h; optical yield given as %ee;	A 18% B 13% C 35%

(RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone (28227-35-2) → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With yeast lipase; butan-1-ol In di-isopropyl ether at 30℃; for 336h; Title compound not separated from byproducts;
With sodium phosphate buffer; esterase B from Candida antarctica In water at 37℃; for 1h; pH=7.3; Product distribution;

pantothenic acid (79-83-4) → (R)-Pantolacton (599-04-2) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
With pantothenase UK-1 at 25℃; Equilibrium constant;

DL-sodium pantoate (1902-01-8) → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With (+)-10-camphorsulfonic acid In various solvent(s) in 99.5 percent EtOH; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With (1S)-(+)-camphorsulfonic acid monohydrate In various solvent(s) at -78℃; Product distribution; 99.5 percent EtOH;

C22H38N2O8 (144762-89-0) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 90℃; for 12h;

Acetic acid (R)-3-cyano-3-hydroxy-2,2-dimethyl-propyl ester → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(R)-4-Benzyloxy-2-hydroxy-3,3-dimethyl-butyronitrile → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogenchloride at 115℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(R)-4,4-Dimethyl-3-((S)-1-phenyl-ethoxy)-dihydro-furan-2-one → (R)-Pantolacton (599-04-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol

R(-)pantoyllactone-β-D-glucopyranoside (171884-77-8) → (R)-Pantolacton (599-04-2)

Conditions	Yield
With ammonium sulfate; potassium phosphate buffer In water Ambient temperature; β-glucosidase presence;

(R)-(1-naphthyl)-glycyl-(R)-phenylglycine (160289-70-3) + pantolactone (79-50-5) → (R)-Pantolacton (599-04-2) + (R)-((R)-2-Amino-2-naphthalen-1-yl-acetylamino)-phenyl-acetic acid; compound with (S)-3-hydroxy-4,4-dimethyl-dihydro-furan-2-one + (R)-((R)-2-Amino-2-naphthalen-1-yl-acetylamino)-phenyl-acetic acid; compound with (R)-3-hydroxy-4,4-dimethyl-dihydro-furan-2-one

Conditions	Yield
In methanol Ambient temperature; Yield given; Title compound not separated from byproducts;

3-diphenylsilanyloxy-4,4-dimethyl-dihydro-furan-2-one → (S)-pantolactone (79-50-5, 599-04-2, 5405-40-3, 52126-90-6) + (R)-Pantolacton (599-04-2)

Conditions	Yield
With toluene-4-sulfonic acid In methanol Hydrolysis; Title compound not separated from byproducts;

trifluoromethylsulfonic anhydride (358-23-6) + (R)-Pantolacton (599-04-2) → (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate (157717-57-2)

Conditions	Yield
With pyridine In dichloromethane at -78 - 23℃; for 3.5h; Inert atmosphere;	100%
With pyridine In dichloromethane at 20℃; for 19.0667h; Inert atmosphere; Cooling with acetone-dry ice;	98%
In pyridine; dichloromethane at -78 - 20℃; for 1.16667h; Inert atmosphere;	96%

benzoyl chloride (98-88-4) + (R)-Pantolacton (599-04-2) → (R)-benzoic acid 4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl ester

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 0.5h;	100%
With dmap; triethylamine In dichloromethane at 0 - 5℃;	90.59%

ethylenediamine (107-15-3) + (R)-Pantolacton (599-04-2) → (2R)-N-(2-aminoethyl)-2,4-dihydroxy-3,3-dimethylbutyramide (616235-99-5)

Conditions	Yield
at 55℃;	100%
In ethanol at 120℃; for 2h; Microwave irradiation;	37%
at 55℃;

methylamine (74-89-5) + (R)-Pantolacton (599-04-2) → (R)-2,4-dihydroxy-N-3,3-trimethylbutanamide (88308-84-3)

Conditions	Yield
In methanol; water at 25℃; for 3h; Inert atmosphere;	100%
In methanol at 20℃; for 3h; Inert atmosphere;	97%

4-methoxybenzyl-2,2,2-trichloroacetimidate + (R)-Pantolacton (599-04-2) → (3R)-3-(4-methoxybenzyloxy)-4,4-dimethyltetrahydrofuran-2-one

Conditions	Yield
With trifluorormethanesulfonic acid In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;	100%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (R)-Pantolacton (599-04-2) → (R)-4,4-dimethyl-3-((triisopropylsilyl)oxy)dihydrofuran-2(3H)-one

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 20℃; for 96h; Inert atmosphere;	100%

(R)-Pantolacton (599-04-2) + 4-amino-n-butyric acid (56-12-2) → hopantenic acid (18679-90-8)

Conditions	Yield
Stage #1: 4-amino-n-butyric acid With sodium hydroxide In water Stage #2: (R)-Pantolacton at 130℃; for 17h; Inert atmosphere;	99%
With triethylamine In methanol at 65℃; for 24h; Inert atmosphere;	89%
With diethylamine In methanol at 60℃;	53%
With sodium methylate
With diethylamine In methanol

(R)-Pantolacton (599-04-2) + 6-aminohexanoic acid (60-32-2) → N-((R)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl)-6-aminohexanoic acid

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In methanol at 26℃; for 40h;	99%
With diethylamine In methanol

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-Pantolacton (599-04-2) → 3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one (133094-78-7)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	99%
With 1H-imidazole In tetrahydrofuran at 20℃; for 24h; Substitution;	97%

(R)-Pantolacton (599-04-2) → (R)-2,4-Dihydroxy-3,3-dimethylbutyramide (27778-35-4)

Conditions	Yield
With ammonia Inert atmosphere;	99%
With ammonia In methanol at 20℃; for 24h;	99%
at 20 - 60℃; for 6h;	95%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (R)-Pantolacton (599-04-2) → (R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on (20374-33-8)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 15h;	98%
With trifluorormethanesulfonic acid In hexane; dichloromethane for 1h;	83%
With trifluorormethanesulfonic acid In dichloromethane benzylation;

dimethyl amine (124-40-3) + (R)-Pantolacton (599-04-2) → D(-)2R,4-dihydroxy-3,3-dimethyl-N,N-dimethyl-butyramide

Conditions	Yield
In ethanol for 72h;	98%

monochloromethanesulfonyl chloride (3518-65-8) + (R)-Pantolacton (599-04-2) → Chloro-methanesulfonic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (182243-70-5)

Conditions	Yield
With pyridine at 0 - 20℃; for 0.166667h;	98%

(R)-Pantolacton (599-04-2) → (2R)-(-)-3,3-dimethylbutane-1,2,4-triol (60856-63-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	97%
Stage #1: (R)-Pantolacton With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Stage #2: With sulfuric acid; sodium sulfate In tetrahydrofuran; water pH=Ca. 3;	88%
Stage #1: (R)-Pantolacton With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃;	82%

(S)-1-phenyl-ethylamine (2627-86-3) + (R)-Pantolacton (599-04-2) → (R)-2,4-Dihydroxy-3,3-dimethyl-N-((S)-1-phenyl-ethyl)-butyramide

Conditions	Yield
With triethylamine In ethanol for 7h; Heating;	97%

methyl 3-aminopropanoate hydrochloride (3196-73-4) + (R)-Pantolacton (599-04-2) → C8H15NO5

Conditions	Yield
Stage #1: methyl 3-aminopropanoate hydrochloride With diethylamine In methanol at 0℃; for 0.25h; Inert atmosphere; Stage #2: (R)-Pantolacton In methanol at 60℃; for 20h; Inert atmosphere;	97%

(1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + (R)-Pantolacton (599-04-2) → (R)-2,4-dihydroxy-N-<(1R)-2-endo-hydroxy-3-endo-bornyl>-3,3-dimethylbutyramide (107730-03-0)

Conditions	Yield
In ethanol at 78℃; for 3h;	96.2%

4-methyleneoxetan-2-one (674-82-8) + (R)-Pantolacton (599-04-2) → (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl 3-oxobutanoate (186899-17-2)

Conditions	Yield
With sodium acetate In acetonitrile for 2h; Heating;	96%

chloromethyl methyl ether (107-30-2) + (R)-Pantolacton (599-04-2) → 3R-(-)-dihydro-4,4-dimethyl-3-<(methoxymethyl)oxy>-2(3H)-furanone (165450-30-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 20h;	96%
With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene at 0℃; for 24h; Reflux;	95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;	90%
With sodium hydride In tetrahydrofuran for 1h; Ambient temperature;	89%
With lithium diisopropyl amide In dichloromethane Ambient temperature;	75%

cyanomethylene triphenylphosphorane (16640-68-9) + (R)-Pantolacton (599-04-2) → [(R)-3-Hydroxy-4,4-dimethyl-dihydro-furan-(2E)-ylidene]-acetonitrile

Conditions	Yield
In toluene for 0.0666667h; Condensation; Irradiation;	96%

p-toluenesulfonyl chloride (98-59-9) + (R)-Pantolacton (599-04-2) → O-(toluene-4-sulfonyl)-D-pantolactone (20374-31-6)

Conditions	Yield
dmap In pyridine Ambient temperature;	95%
With pyridine

propan-1-ol-3-amine (156-87-6) + (R)-Pantolacton (599-04-2) → pantothenol (81-13-0)

Conditions	Yield
With triethylamine In ethanol at 160℃; for 3h; Microwave irradiation;	95%
With methanol
at 60℃; for 5h;

n-Dodecylamine (124-22-1) + (R)-Pantolacton (599-04-2) → (2R)-N-Dodecyl-2,4-dihydroxy-3,3-dimethylbutanamid (117801-01-1)

Conditions	Yield
at 115℃; for 3h;	95%

(E)-2-oxo-4-phenyl-3-butenoic acid (1914-59-6) + (R)-Pantolacton (599-04-2) → (E)-2-Oxo-4-phenyl-but-3-enoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃;	95%

(R)-Pantolacton (599-04-2) + 6,8-dimethoxy-3-(1-methyl-2-oxo-vinyl)-isochromen-1-one (447407-66-1) → (R)-2-(6,8-Dimethoxy-1-oxo-1H-isochromen-3-yl)-propionic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (447407-65-0)

Conditions	Yield
at -40℃; for 1.66667h;	95%

4-(methylthio)benzylamine (83171-39-5) + (R)-Pantolacton (599-04-2) → (R)-(+)-2,4-dihydroxy-3,3-dimethyl-N-(4-methyl-sulfanyl-benzyl)butyramide (1227380-62-2)

Conditions	Yield
In toluene at 65℃; Inert atmosphere;	95%

Upstream product

• 13031-04-4 ketopantolactone 
• 82118-78-3 (2S)-3,3-Dimethylbernsteinsaeure-4-methylester 
• 157717-57-2 (3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate 
• 250738-86-4 tert-butyl-(4,4-dimethyl-4,5-dihydro-furan-2-yloxy)-dimethyl-silane 
• 28227-35-2 (RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 
• 75-36-5 acetyl chloride 
• 924-44-7 glyoxylic acid ethyl ester 
• 78-84-2 isobutyraldehyde 
• 895532-73-7 (S)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol 
• 1377411-53-4 (S)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropyl acetate 
• 1377411-54-5 (3S,4R)-3-(benzyloxy)-4,5-dihydroxy-2,2-dimethylpentyl acetate 
• 1377411-55-6 (S)-3-(benzyloxy)-2,2-dimethyl-4-oxobutyl acetate 
• 1377411-56-7 (2S)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoic acid 
• 1377411-48-7 ethyl (S)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate 

Downstream Products

• 134734-33-1 O-(4-nitro-benzoyl)-L-pantolactone 
• 101776-81-2 N-phenethyl-L-pantamide 
• 20664-72-6 O-(toluene-4-sulfonyl)-L-pantolactone 
• 55512-69-1 pantetheine 
• 138148-35-3 D-pantethine 
• 50692-78-9 methyl 3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoate 
• 32344-71-1 D-pantothenic acid-(2-benzylsulfanyl-ethylamide) 
• 74920-83-5 N-(3-oxo-3-phenyl-propyl)-D-pantamide 
• 51250-36-3 (R)-2.4-dihydroxy-3.3-dimethyl-N-(2-phenylsulfamoyl-ethyl)-butyramide 
• 1262977-05-8 (R)-2.4-dihydroxy-3.3-dimethyl-N-[2-(4-chloro-phenylsulfamoyl)-ethyl]-butyramide 
• 27824-25-5 (R)-2,4-dihydroxy-3,3-dimethyl-N-(3-oxo-3-(phenylamino)propyl)butanamide 
• 85508-39-0 D-pantothenic acid-((1R)-menthyl ester) 
• 85508-39-0 D-pantothenic acid-((1S)-menthyl ester) 
• 28227-36-3 (R)-acetic acid 4,4-dimethyl-2-oxo-tetrahydrofuran-3-yl ester 

Relevant articles and documents

R(-)PANTOYLLACTONE-β-D-GLUCOPYRANOSIDE: CHARACTERIZATION OF A METABOLITE FROM RICE SEEDLINGS

A new derivative of pantoic acid, R(-)pantoyllactone-β-D-glucopyranoside, has been isolated from rice seedlings and its structure determined. β-Glucosidase hydrolysed it to D-glucose and R(-)pantoyllactone.Alkaline hydrolysis converted it to the salt of 2-R(-)pantoic acid β-D-glucopyranoside.It accumulated in rice shoots but not in roots. - Keywords: Oryza sativa; Gramineae; rice seedling; pantoyllactone glucoside; pantoic acid glucoside; new metabolite; NMR signal assignment; shoot to root distribution.

Copper-Mediated Synthesis of N-Acyl Vinylogous Carbamic Acids and Derivatives: Synthesis of the Antibiotic CJ-15,801

(Equation presented) Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.

Synthesis of (R)-pantoyl lactone by reduction of ketopantoate with formate and Proteus species

(R)-Pantoyl lactone (ee > 97%) is obtained by stereoselective reduction of ketopantoate with resting cells of anaerobically grown Proteus vulgaris or Proteus mirabilis. Benzyl-viologen or safranine T have been used as electron mediators.

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Optical Resolution of (R,S)-Pantolactone through Amide Formation

The optical resolution of (RS)-pantolactone (1) is carried out through formation of diastereomeric amides.These are separated by a single hot washing with CH2Cl2 or CHCl3.The used asymmetric amine, (1R)-3-endo-aminoborneol (4), is readily accessible and can be recovered almost quantitatively after resolution.

Industrial kinetic resolution ofd,l-pantolactone by an immobilized whole-cell biocatalyst

Immobilized whole-cells ofPichia pastorisharboring recombinantd-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution ofd,l-pantolactone. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis ofd-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.

Synthesis method of chiral 2-hydroxy-1, 4-dicarbonyl compound and pantoic acid lactone

The invention discloses a chiral 2-hydroxy-1, 4-dicarbonyl compound synthesized by catalyzing asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate by taking tetrapeptide TP or an enantiomer ent-TP thereof as a chiral catalyst, and application of a synthetic product. The method for synthesizing the chiral 2-hydroxy-1, 4-dicarbonyl compound through the asymmetric Aldol reaction is shown as a formula 1 and a formula 2. The asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate is catalyzed to synthesize the optically active 2-hydroxy-1, 4-dicarbonyl compound, then the optically active pantoic acid lactone can be further synthesized, and the method has advantages of mild reaction conditions, easy operation, low catalyst consumption, high yield and the like, and can synthesize the 2-hydroxy-1, 4-dicarbonyl compounds with two configurations by using tetrapeptide and the enantiomerthereof.

Peptide-Catalyzed Highly Asymmetric Cross-Aldol Reaction of Aldehydes to Biomimetically Synthesize 1,4-Dicarbonyls

β-Turn tetrapeptides were demonstrated to catalyze asymmetric aldol reaction of α-branched aldehydes and α-carbonyl aldehydes, i.e. glyoxylates and α-ketoaldehydes, to biomimetically synthesize acyclic all-carbon quaternary center-bearing 1,4-dicarbonyls in high yield and excellent enantioselectivity under mild conditions. The spatially restricted environment of the tetrapeptide warrants high enantioselectivity and yield with broad substrates. Using this protocol, (R)-pantolactone, the key intermediate of vitamin B5, was readily accessed in a practical, efficient, and environmentally benign process from inexpensive starting materials.