2217-15-4

Basic information

• Product Name: (+)-Diisopropyl L-tartrate
• Synonyms: 2,3-dihydroxy-(R-(R*,R*))-butanedioicacid,bis(1-methylethyl)ester;2,3-dihydroxy-R-R*,R*-butanedioicacid,bis1-methylethylester;2,3-dihydroxy-succinicaciddiisopropylester;Lg-tartaricaciddiisopropylester;Lg-threaricaciddiisopropylester;Tartaricacid,diisopropylester;tartaricaciddiisopropylester;(+)-Diisopropyl L-tartrate,99%
• CAS NO: 2217-15-4
• Molecular Formula: C₁₀H₁₈O₆
• Molecular Weight: 234.25
• EINECS: 218-709-0
• Product Categories: chiral;API intermediates;Asymmetric Synthesis;Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound
• Mol File: 2217-15-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 152 °C12 mm Hg(lit.)
• Flash Point: 229 °F
• Appearance: Clear colorless/Viscous Liquid
• Density: 1.114 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.70±0.20(Predicted)
• Sensitive: Hygroscopic
• BRN: 1727863
• CAS DataBase Reference: (+)-Diisopropyl L-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Diisopropyl L-tartrate(2217-15-4)
• EPA Substance Registry System: (+)-Diisopropyl L-tartrate(2217-15-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• RTECS: WW8100000
• Hazardous Substances Data: 2217-15-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 2217-15-4 differently. You can refer to the following data:
1. (+)-Diisopropyl L-Tartrate is a reagent for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation.
2. Both D- and L-forms are reagents for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation.

InChI:InChI=1/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m1/s1

Synthetic route

diethyl (2R,3R)-tartrate (87-91-2) + isopropyl alcohol (67-63-0) → L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
With indium; iodine for 7h; transesterification; Heating;	87%

tartaric acid (87-69-4) + isopropyl alcohol (67-63-0) → L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
With calcium chloride

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + pinanediol (18680-27-8) → L-(+)-diisopropyl tartrate (2217-15-4) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.25h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + trimethyleneglycol (504-63-2) → 2-Phenyl-1,3,2-dioxaborinane (4406-77-3) + L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A 99 % Spectr. B n/a

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → L-(+)-diisopropyl tartrate (2217-15-4) + 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane (5123-13-7)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2,4-dimethylpentane-2,4-diol (24892-49-7, 139687-48-2) → L-(+)-diisopropyl tartrate (2217-15-4) + 2,4-dimethyl-2,4-pentanediol phenylboronic ester (95843-97-3)

Conditions	Yield
In chloroform-d1 at 20℃; for 3h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2,2'-iminobis[ethanol] (111-42-2) → L-(+)-diisopropyl tartrate (2217-15-4) + diethanolamine phenylboronic ester (4406-73-9)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + N-tert-butyldiethanolamine (2160-93-2) → L-(+)-diisopropyl tartrate (2217-15-4) + N-tert-butyldiethanolamine phenylboronic ester (73029-08-0)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2.6-bis(hydroxymethyl)pyridine (1195-59-1) → 2,6-pyridinedimethanol phenylboronic ester + L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A 90 % Spectr. B n/a

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + (2S,3S)-butane-2,3-diol (19132-06-0) → (4S,5S)-4,5-dimethyl-2-phenyl-1,3,2-dioxaborolane + L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A 98 % Spectr. B n/a

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → L-(+)-diisopropyl tartrate (2217-15-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Conditions	Yield
In chloroform-d1 at 20℃; for 48h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + cis-1,2-cyclohexane (1792-81-0) → L-(+)-diisopropyl tartrate (2217-15-4) + (3aR,7aS)-2-phenyl-hexahydro-2H-1,3,2-benzodioxaborole (6638-70-6)

Conditions	Yield
In chloroform-d1 at 20℃; for 20h; Title compound not separated from byproducts.;	A n/a B 92 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + cis-1,2-cyclopentanediol (5057-98-7) → L-(+)-diisopropyl tartrate (2217-15-4) + (3aR,6aS)-2-phenyl-hexahydrocyclopenta[d][1,3,2]dioxaborole (7462-37-5)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.25h; Title compound not separated from byproducts.;	A n/a B 99 % Spectr.

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + ethylene glycol (107-21-1) → 2-phenyl[1,3,2]dioxaborolane (4406-72-8) + L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
In chloroform-d1 at 20℃; for 0.1h; Title compound not separated from byproducts.;	A 99 % Spectr. B n/a

L-Tartaric acid (87-69-4) + isopropyl alcohol (67-63-0) → L-(+)-diisopropyl tartrate (2217-15-4)

Conditions	Yield
With thionyl chloride at 20℃;

L-(+)-diisopropyl tartrate (2217-15-4) → (4R,5R)-2-Oxo-2λ4-[1,3,2]dioxathiolane-4,5-dicarboxylic acid diisopropyl ester (136029-38-4)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 50℃; for 1h;	100%
With thionyl chloride In tetrachloromethane for 1h; Heating;	96%
With pyridine; thionyl chloride In dichloromethane at 0℃;

L-(+)-diisopropyl tartrate (2217-15-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-succinic acid diisopropyl ester (147488-89-9)

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

L-(+)-diisopropyl tartrate (2217-15-4) → (2R)-diisopropyl 2-hydroxybutanedioate (83540-97-0)

Conditions	Yield
With samarium diiodide; ethylene glycol In tetrahydrofuran for 1h; Ambient temperature;	99%

(E)-crotylboronate diethanolamine complex + L-(+)-diisopropyl tartrate (2217-15-4) → (R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate (99687-40-8, 106357-20-4, 106357-33-9, 99745-86-5)

Conditions	Yield
With sodium chloride In diethyl ether stirred under nitrogen for 5 min; extraction of aqueous layer with Et2O; organic extracts combined; dried over MgSO4; filtration; concn.;	99%

L-(+)-diisopropyl tartrate (2217-15-4) + benzoic acid hydrazide (613-94-5) → (benzoylhydrazono)acetic acid isopropyl ester

Conditions	Yield
Stage #1: L-(+)-diisopropyl tartrate With sodium periodate In water at 0℃; for 2h; Stage #2: benzoic acid hydrazide In ethanol for 12h;	99%

L-(+)-diisopropyl tartrate (2217-15-4) + 2,2-dimethoxy-propane (77-76-9) → diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate (81327-47-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 3h; Heating;	97%
In various solvent(s) Heating;	82%

L-(+)-diisopropyl tartrate (2217-15-4) + allyl bromide (106-95-6) → (2R,3R)-2,3-Bis-allyloxy-succinic acid diisopropyl ester

Conditions	Yield
Stage #1: L-(+)-diisopropyl tartrate With sodium hydride In tetrahydrofuran at 0 - 25℃; for 1h; Metallation; Stage #2: allyl bromide With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 25℃; for 4h; Etherification;	97%

chloro-trimethyl-silane (75-77-4) + L-(+)-diisopropyl tartrate (2217-15-4) → Di(1-methylethyl)-(2R,3R)-2,3-bis<(trimethylsilyl)oxy>butandioat (130678-42-1)

Conditions	Yield
With triethylamine In dichloromethane a) 0 deg C, 10 min, b) r.t., 5h;	96%

L-(+)-diisopropyl tartrate (2217-15-4) + Triethyl orthoacetate (78-39-7) → diisopropyl (4R,5R)-2-ethoxy-2-methyl-1,3-dioxolan-4,5-dicarboxylate (130258-01-4)

Conditions	Yield
With sulfuric acid at 130℃; for 3h;	96%

L-(+)-diisopropyl tartrate (2217-15-4) → isopropyl glyoxalate (924-53-8)

Conditions	Yield
With sodium periodate In diethyl ether; water at 0℃; for 2.33333h;	95%
With sodium periodate In water at 0℃; for 2h; Inert atmosphere;	60%
With sodium periodate at 0℃; for 2h;

L-(+)-diisopropyl tartrate (2217-15-4) + trans-cinnamaldehyde diethylacetal (25226-98-6) → (4R,5R)-4,5-Bis((2-methylethoxy)carbonyl)-2-(trans-2-phenylethenyl)-1,3-dioxolane (99267-72-8)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 1h; Heating;	93%

bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5) + L-(+)-diisopropyl tartrate (2217-15-4) → Zr2O2(C5H5)4(C2H2O(CO2CH(CH3)2)2)2

Conditions	Yield
In dichloromethane evapd., twice recrystd. from toluene;;	93%

L-(+)-diisopropyl tartrate (2217-15-4) + benzyl bromide (100-39-0) → *,R*)>-bis(1-methylethyl) 2,3-bis(phenylmethoxy)butanedioate (139631-40-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	92%

L-(+)-diisopropyl tartrate (2217-15-4) → dihydroxyacetic acid isopropyl ester (188691-14-7)

Conditions	Yield
With sodium periodate; silica gel In dichloromethane for 1.5h; Ambient temperature;	90%

L-(+)-diisopropyl tartrate (2217-15-4) + orthoformic acid triethyl ester (122-51-0) → diisopropyl (4R,5R)-2-ethoxy-1,3-dioxolan-4,5-dicarboxylate

Conditions	Yield
With sulfuric acid at 130℃; for 3h;	88%

L-(+)-diisopropyl tartrate (2217-15-4) + 3-Phenylpropenol (104-54-1) → 3-phenyl-(2R,3R)-oxiran-2-ylmethanol (98819-68-2)

Conditions	Yield
Stage #1: L-(+)-diisopropyl tartrate With titanium(IV) isopropylate In dichloromethane at 300℃; for 0.0833333h; Inert atmosphere; Molecular sieve; Stage #2: 3-Phenylpropenol In dichloromethane for 1h; Inert atmosphere;	88%

L-(+)-diisopropyl tartrate (2217-15-4) + allyl halide → (2R,3R)-2,3-Bis-allyloxy-succinic acid diisopropyl ester

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	86%

L-(+)-diisopropyl tartrate (2217-15-4) + methyl halide → (+)-O.O-Dimethyl-weinsaeurediisopropylester

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	85%

L-(+)-diisopropyl tartrate (2217-15-4) + (Z)-crotylboronate diethanolamine complexes → (R,R)-diisopropyl tartrate (Z)-crotylboronate (106357-20-4)

Conditions	Yield
With sodium chloride In diethyl ether; water	85%

L-(+)-diisopropyl tartrate (2217-15-4) + (E)-crotylboronate diethanolamine complexes → (R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate (99687-40-8, 106357-20-4, 106357-33-9, 99745-86-5)

Conditions	Yield
With sodium chloride In diethyl ether; water	85%

L-(+)-diisopropyl tartrate (2217-15-4) + chloroacetyl chloride (79-04-9) → (2R,3R)-2,3-Bis-(2-chloro-acetoxy)-succinic acid diisopropyl ester (226710-52-7)

Conditions	Yield
With pyridine In chloroform for 5h; Ambient temperature;	84%

L-(+)-diisopropyl tartrate (2217-15-4) + Benzoyl isothiocyanate (532-55-8) → (4R,5R)-4,5-di(isopropyloxycarbonyl)-3-benzoyloxazolidin-2-one (253350-02-6)

Conditions	Yield
Stage #1: L-(+)-diisopropyl tartrate With di(n-butyl)tin oxide In 1,2-dichloro-ethane for 4h; Heating; Stage #2: Benzoyl isothiocyanate With triethylamine In 1,2-dichloro-ethane for 1h; Heating; Stage #3: With tetrabutylammomium bromide In 1,2-dichloro-ethane for 2h; Heating; Further stages.;	84%

L-(+)-diisopropyl tartrate (2217-15-4) + 2-bromomethylnaphthyl bromide (939-26-4) → (2R,3R)-2,3-Bis-(naphthalen-2-ylmethoxy)-succinic acid diisopropyl ester

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	83%

L-(+)-diisopropyl tartrate (2217-15-4) + [(1E)-3-phenylprop-1-en-1-yl]boronic acid (129423-29-6) → (4R,5R)-diisopropyl 2-((E)-3-phenylprop-1-enyl)-1,3,2-dioxaborolane-4,5-dicarboxylate

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	83%

L-(+)-diisopropyl tartrate (2217-15-4) + α.ε.ι-trimethyl-undecylaldehyde (105-88-4) → Di(1-methylethyl)-(4R,5R)-2-<(1RS,5RS)-1,5,9-trimethyldecyl>-1,3-dioxolan-4,5-dicarboxylat (130678-57-8, 130793-54-3, 130793-55-4, 130793-59-8)

Conditions	Yield
toluene-4-sulfonic acid In toluene Heating;	82%

L-(+)-diisopropyl tartrate (2217-15-4) + trimethyl orthoformate (149-73-5) → (4R,5R)-di-isopropyl-2-methoxy-1,3-dioxolane-4,5-dicarboxylate (649721-37-9)

Conditions	Yield
With sulfuric acid In toluene Heating;	81%

L-(+)-diisopropyl tartrate (2217-15-4) + phenylboronic acid (98-80-6) → (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1)

Conditions	Yield
In toluene byproducts: H2O; addn. of diisopropyl tartrate to toluene soln. of boronic acid deriv., refluxing for 24 h in Dean-Stark app.; cooling to room temp., drying, filtration, evapn. in vac., recrystn. (hexane), elem. anal.;	81%
In pentane at 20℃;

L-(+)-diisopropyl tartrate (2217-15-4) + triethoxymethylbenzene (1663-61-2) → diisopropyl (4R,5R)-2-ethoxy-2-phenyl-1,3-dioxolan-4,5-dicarboxylate

Conditions	Yield
With sulfuric acid at 130℃; for 3h;	80%

L-(+)-diisopropyl tartrate (2217-15-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2R,3R)-2-Hydroxy-3-triisopropylsilanyloxy-succinic acid diisopropyl ester

Conditions	Yield
With 2,5-dimethylpyridine In dichloromethane at 21℃;	80%

Upstream product

• 87-69-4 L-Tartaric acid 
• 67-63-0 isopropyl alcohol 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 107-21-1 ethylene glycol 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 1792-81-0 cis-1,2-cyclohexane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 19132-06-0 (2S,3S)-butane-2,3-diol 
• 1195-59-1 2.6-bis(hydroxymethyl)pyridine 
• 2160-93-2 N-tert-butyldiethanolamine 
• 111-42-2 2,2'-iminobis[ethanol] 
• 24892-49-7 2,4-dimethylpentane-2,4-diol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 504-63-2 trimethyleneglycol 

Downstream Products

• 139631-40-6 *,R^*)>-bis(1-methylethyl) 2,3-bis(phenylmethoxy)butanedioate 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 24347-58-8 (R,R)-2,3-butandiol 
• 99267-80-8 (4R,5R)-2-((1R,2R)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester 
• 547765-85-5 ((CH₃)2CHOOC)2(C₆H₅)4C₂H₂O₂P₂PtCl₂ 
• 875272-65-4 (4R,5R)-2-((E)-Styryl)-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester 
• 141783-42-8 (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 99267-72-8 (4R,5R)-4,5-Bis((2-methylethoxy)carbonyl)-2-(trans-2-phenylethenyl)-1,3-dioxolane 
• 69036-26-6 (S)-1-cyclohexylbut-3-en-1-ol 
• 100-49-2 cyclohexylmethyl alcohol 

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