87-91-2

Basic information

• Product Name: L(+)-Diethyl L-tartrate
• Synonyms: (+)-DIETHYL L-TARTRATE;DIETHYL L-(+)-TARTRATE;DIETHYL L-TARTRATE;DIETHYL-L-TARTRATE, (+)-;DIETHYL TARTRATE;(+)-DIETHYL-2,3-DIHYDROXYSUCCINATE;(+)-DIETHYL1-2,3-DIHYDROXYSUCCINATE;DET
• CAS NO: 87-91-2
• Molecular Formula: C₈H₁₄O₆
• Molecular Weight: 206.19
• EINECS: 201-783-3
• Product Categories: Pharmaceutical Intermediates;Chiral Compounds;chiral;Asymmetric Synthesis;Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound
• Mol File: 87-91-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 17 °C
• Boiling Point: 280 °C(lit.)
• Flash Point: 200 °F
• Appearance: Clear/Viscous Liquid
• Density: 1.204 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000467mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Water (Slightly)
• PKA: 11.61±0.20(Predicted)
• Water Solubility: insoluble
• Merck: 14,3855
• BRN: 1727145
• CAS DataBase Reference: L(+)-Diethyl L-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: L(+)-Diethyl L-tartrate(87-91-2)
• EPA Substance Registry System: L(+)-Diethyl L-tartrate(87-91-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 87-91-2(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 87-91-2 differently. You can refer to the following data:
1. Diethyl tartrate has a mild, fruity, wine aroma.
2. Colorless to light yellow liqui

Occurrence

The d-isomer has not been reported found in nature; the l-isomer and the racemic form are of little importance. Reported found in sherry, white and red wine.

Uses

Different sources of media describe the Uses of 87-91-2 differently. You can refer to the following data:
1. (+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.
2. (+)-Diethyl L-tartrate can be used in the synthesis of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E.
3. Diethyl L-(+)-Tartrate is used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke thera py.

General Description

Made from natural tartaric acid

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1

Synthetic route

ethanol (64-17-5) + L-Tartaric acid (87-69-4) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
With thionyl chloride	100%
With methanesulfonic acid at 30 - 35℃; for 12h;	99%
With thionyl chloride at 0 - 50℃; for 3.5h; Temperature;	96.2%

ethanol (64-17-5) + (R,R)-tartaric acid ethyl ester (608-89-9) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
at 160℃;

ethyl iodide (75-03-6) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
With silver tartrate

ethanol (64-17-5) + tartaric acid (87-69-4) → diethyl (2R,3R)-tartrate (87-91-2)

diethyl Fumarate (623-91-6) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
With diethyl ether; dihydrogen peroxide Irradiation.mit rechts-zirkular polarisiertem UV-Licht entsteht ein schwach rechtsdrehendes Praeparat;

ethanol (64-17-5) + dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
In various solvent(s) at 39℃; for 168h; lipase from Pseudomonas fluorescens;	96.5 % Spectr.

ethanol (64-17-5) + L-Tartaric acid (87-69-4) + dehydrocholic acid (81-23-2) → diethyl (2R,3R)-tartrate (87-91-2) + 3,7,12-trioxo-5β-cholan-24-oic acid ethyl ester (52718-49-7)

Conditions	Yield
With methanesulfonic acid for 5 - 6h; Heating / reflux;

octanol (111-87-5) + C12H24Cl2O6Si2 → diethyl (2R,3R)-tartrate (87-91-2) + dimethyl-bis-octyloxy-silane (18536-88-4) + chloro(dimethyl)octyloxysilane (52322-14-2)

Conditions	Yield
With gallium(III) trichloride at 20℃; for 6h; Inert atmosphere;

(+/-)-diethyl tartrate (57968-71-5) → diethyl (2S,3S)-tartrate (13811-71-7) + diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
With (S)-aminopropyl alcohol(at)silica 1 In hexane; isopropyl alcohol at 20℃; for 1h; Purification / work up; Resolution of racemate; Inert atmosphere;	A n/a B n/a

L-Tartaric acid (87-69-4) → diethyl (2R,3R)-tartrate (87-91-2)

Conditions	Yield
With hydrogenchloride In ethanol

diethyl (2R,3R)-tartrate (87-91-2) + dimethyl sulfate (77-78-1) → (+)-(2R,3R)-diethyl di-O-methyltartrate (27957-93-3)

Conditions	Yield
With sodium hydride In diethyl ether at 0 - 20℃; Inert atmosphere;	100%
With sodium hydride In diethyl ether at 0 - 20℃; Inert atmosphere;	100%
With sodium hydride In diethyl ether at 0 - 20℃;	100%
With sodium hydride In diethyl ether

Trimethyl orthoacetate (1445-45-0) + diethyl (2R,3R)-tartrate (87-91-2) → diethyl (4R)-trans-2-methoxy-2-methyl-1,3-dioxolan-4,5-dicarboxylate (134745-01-0)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 12h;	100%
With sulfuric acid In benzene at 80℃;	98%

Dimethoxymethane (109-87-5) + diethyl (2R,3R)-tartrate (87-91-2) → (+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate (100449-52-3)

Conditions	Yield
With phosphorus pentaoxide In chloroform for 2.5h; Ambient temperature;	100%
With phosphorus pentoxide In dichloromethane for 5h; Ambient temperature;	100%
With phosphorus pentoxide In chloroform for 2h; Alkylation;	97%
With phosphorus pentoxide In dichloromethane	96%
With phosphorus pentoxide In dichloromethane

diethyl (2R,3R)-tartrate (87-91-2) → diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide (136087-36-0)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 50℃; for 1h;	100%
With thionyl chloride In tetrachloromethane for 2h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 50℃; for 2.5h;

diethyl (2R,3R)-tartrate (87-91-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-succinic acid diethyl ester (124224-83-5)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 35℃; for 14h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 12h;	100%
With 1H-imidazole In N,N-dimethyl-formamide	95%

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) + (4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 8h; Heating; Title compound not separated from byproducts.;	A 100% B n/a
for 2.5h; Heating;

Dimethoxymethane (109-87-5) + diethyl (2R,3R)-tartrate (87-91-2) → trans-(4R,5R)-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester (21154-13-2, 60077-28-3, 70561-17-0)

Conditions	Yield
With 3 A molecular sieve; Amberlyst 15 ion-exchange resin In ethyl acetate for 24h; Heating;	100%
With boron trifluoride diethyl etherate In Isopropyl acetate	100%

diethyl (2R,3R)-tartrate (87-91-2) → bis(diethyl-L-tartrateglycolato)diboron

Conditions	Yield
With tetrakis(dimethylamido)diborane In toluene at 105℃; for 0.116667h;	100%

1,1-dimethoxyethylene (922-69-0) + diethyl (2R,3R)-tartrate (87-91-2) → C16H30O10 (1092455-59-8)

Conditions	Yield
at 20℃; for 0.5h; Inert atmosphere; neat (no solvent);	100%

diethyl (2R,3R)-tartrate (87-91-2) + acetone (67-64-1) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8)

Conditions	Yield
With orthoformic acid triethyl ester	99%
With hydrogenchloride; orthoformic acid triethyl ester In N,N-dimethyl-formamide at 20℃; for 72h;	85%
boron trifluoride diethyl etherate at 23℃; for 5.5h; protection;	80%

diethyl (2R,3R)-tartrate (87-91-2) + chloromethyl methyl ether (107-30-2) → (+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate (100449-52-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 10h;	99%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	99%
With N-ethyl-N,N-diisopropylamine In chloroform at 60℃; for 36h;	79%
With N-ethyl-N,N-diisopropylamine for 48h; Ambient temperature;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; for 18h;	130 g

diethyl (2R,3R)-tartrate (87-91-2) + 4-chlorobenzoylmethylenetriphenylphosphorane (1777-56-6) → (E)-ethyl 4-(4-chlorophenyl)-4-oxobut-2-enoate (89781-40-8)

Conditions	Yield
Stage #1: diethyl (2R,3R)-tartrate With periodic acid In diethyl ether at 20 - 25℃; for 3h; Stage #2: 4-chlorobenzoylmethylenetriphenylphosphorane In tetrahydrofuran; diethyl ether at 0 - 25℃; for 16h;	99%

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 8h; Heating;	98%
With toluene-4-sulfonic acid for 8h; Reflux;	98%
With toluene-4-sulfonic acid	97%

diethyl (2R,3R)-tartrate (87-91-2) + butylboronic acid (4426-47-5) → (4R,5S)-2-butyl-4,5-dicarboethoxy-1,3,2-diazaborolane

Conditions	Yield
In benzene equiv. amts. of tratrate and boronic acid were refluxed for 2 h with Dean-Stark trap; distn.; elem. anal.;	98%

bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5) + diethyl (2R,3R)-tartrate (87-91-2) → ((C5H5)2Zr(C2H5OOCCH(O)CH(O)COOC2H5))2

Conditions	Yield
In dichloromethane byproducts: CH4; (N2 or Ar); to a soln. of dimethylzirconocene added dropwise tartrate at room temp. over a period of 0.5 h; stirred for 1 h; evapd.; washed with pentane; dried in vacuo; elem. anal.;	98%

diethyl (2R,3R)-tartrate (87-91-2) → diethyl 2,3-difluorosuccinate (868-24-6)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 90℃; for 5h;	97%

diethyl (2R,3R)-tartrate (87-91-2) + allyl bromide (106-95-6) → (2R,3R)-2,3-Bis-allyloxy-succinic acid diethyl ester (65973-54-8)

Conditions	Yield
With silver(l) oxide In diethyl ether 2 h reflux in the dark, 1-3 d stirring;	97%
With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 0 - 25℃; for 4h; Etherification;	93%
With sodium hydride In tetrahydrofuran	68%
Stage #1: diethyl (2R,3R)-tartrate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: allyl bromide With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 1.5h;

diethyl (2R,3R)-tartrate (87-91-2) + 2-Methoxypropene (116-11-0) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane	97%
With camphor-10-sulfonic acid In toluene at 20℃; for 5h;	74%

diethyl (2R,3R)-tartrate (87-91-2) + methyl iodide (74-88-4) → (+)-(2R,3R)-diethyl di-O-methyltartrate (27957-93-3)

Conditions	Yield
With silver(l) oxide for 19h; Inert atmosphere; Schlenk technique; Reflux;	96%
(i) TlOEt, benzene, (ii) /BRN= 969135/; Multistep reaction;
With silver(l) oxide

diethyl (2R,3R)-tartrate (87-91-2) + orthoformic acid triethyl ester (122-51-0) → L-(R,R)-2-ethoxy-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester (162491-34-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 130 - 140℃; for 2h;	96%
With camphor-10-sulfonic acid In toluene at 95℃;	95%

diethyl (2R,3R)-tartrate (87-91-2) + 1,4-Cyclohexanedione (637-88-7) → tetraethyl (2R,3R,10R,11R)-1,4,9,12-tetraoxadispiro[4.2.48.25]tetradecane-2,3,10,11-tetracarboxylate (216373-63-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 30h; cyclocondensation; Heating;	96%
With toluene-4-sulfonic acid In toluene for 120h; Condensation; Heating;	92%
With boron trifluoride diethyl etherate In ethyl acetate at 0 - 20℃;	55%
With boron trifluoride diethyl etherate In ethyl acetate at 0℃;

3,3-dimethoxypentane (25636-49-1) + diethyl (2R,3R)-tartrate (87-91-2) → diethyl (4R,5R)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate (68572-82-7)

Conditions	Yield
With 4 A molecular sieve; toluene-4-sulfonic acid In benzene for 3h; Heating;	96%

diethyl (2R,3R)-tartrate (87-91-2) → (2R,3R)-2,3-dihydroxybutanedihydrazide (76585-39-2, 80081-45-4, 80081-47-6, 80081-49-8, 54789-92-3)

Conditions	Yield
With hydrazine In ethanol; water Heating / reflux;	96%
With hydrazine hydrate In ethanol for 7h; Reflux;	88%
With hydrazine hydrate In ethanol for 2h; Reflux;	87%

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 50℃; for 9h; Temperature; Reagent/catalyst; Reflux;	95.5%
toluene-4-sulfonic acid In benzene for 1h; Heating;	89%
With camphor-10-sulfonic acid

diethyl (2R,3R)-tartrate (87-91-2) + benzylamine (100-46-9) → (2R,3R)-N1,N4-dibenzyl-2,3-dihydroxysuccinamide (88393-56-0)

Conditions	Yield
With potassium carbonate In methanol for 7h; Heating;	95.3%
With potassium carbonate In methanol Inert atmosphere; Reflux;	90%
With potassium carbonate In methanol at 80℃; for 15h; Inert atmosphere;	62.4%

diethyl (2R,3R)-tartrate (87-91-2) + dibromotriphenylphosphorane (1034-39-5) → (4R,5R)-2,2,2-Triphenyl-2λ5-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid diethyl ester

Conditions	Yield
With triethylamine In toluene Cyclization;	95%

diethyl (2R,3R)-tartrate (87-91-2) + ethyl chlorocarbonylacetate (36239-09-5) → 1,1'-[(R,R)-1,2-bis(ethoxycarbonyl)ethane-1,2-diyl] 3,3'-diethyl bis(malonate)

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; for 12h;	95%

methanol (67-56-1) + diethyl (2R,3R)-tartrate (87-91-2) → butanedioic acid, monoethyl ester (1070-34-4)

Conditions	Yield
With potassium perrhenate; phosphoric acid; palladium on activated charcoal; hydrogen; pyrographite at 150℃; under 3878.71 Torr;	95%

diethyl (2R,3R)-tartrate (87-91-2) + chloro-diphenylphosphine (1079-66-9) → (2R,3R)-2,3-O-Bis(diphenylphosphinoxy)weinsaeurediethylester (102139-89-9)

Conditions	Yield
With pyridine In diethyl ether at 20℃; for 4h;	94%
With dmap In toluene at 20℃; for 3h; Substitution;

Upstream product

• 75-03-6 ethyl iodide 
• 64-17-5 ethanol 
• 87-69-4 L-tartaric acid 
• 147-71-7 D-tartaric acid 
• 57968-71-5 (+/-)-diethyl tartrate 
• 111-87-5 octanol 
• 87-69-4 L-Tartaric acid 
• 81-23-2 dehydrocholic acid 
• 622-00-4 dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 
• 623-91-6 diethyl Fumarate 
• 87-69-4 tartaric acid 
• 608-89-9 (R,R)-tartaric acid ethyl ester 

Downstream Products

• 61045-33-8 diethyl (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate 
• 451472-23-4 2,3-diethyl(2R,3R)-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate 
• 102921-23-3 (+)-2-O-<4-(Phenylazo)benzoyl>weinsaeure-diethylester 
• 102921-21-1 (-)-2,3-Bis-O-<4-(phenylazo)benzoyl>weinsaeure-diethylester 
• 77312-71-1 diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate 
• 119770-87-5 (2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate 
• 62243-26-9 Diethyl α,β-dichlorosuccinate 
• 110590-88-0 bis-phenylhydrazono-succinic acid diethyl ester 
• 137585-08-1 tetraethyl 2,2'-(benzene-1,4-diyl)bis[(4R,5R)-1,3-dioxolane-4,5-dicarboxylate] 
• 1180511-25-4 (2R,3R)-1,1,4,4-tetrakis(3-methylphenyl)butane-1,2,3,4-tetraol 
• 1180511-15-2 (2R,3R)-1,1,4,4-tetrakis(2-methylphenyl)butane-1,2,3,4-tetraol 
• 594845-76-8 (R)-2-benzyloxyethyl-5-oxotetrahydrofuran-2-carboxylic acid 
• 21461-89-2 (S)-(-)-tetrahydro-2-methyl-5-oxo-2-furancarboxylic acid 
• 21461-86-9 (5R)-γ-valerolactone γ-carboxylic acid 

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