(-)-Di-p-toluoyl-L-tartaric acid supplier

Name
(-)-Di-p-toluoyl-L-tartaric acid
EINECS 251-131-7
CAS No. 32634-66-5
Article Data10
CAS DataBase
Density 1.371 g/cm³
Solubility soluble
Melting Point 169-171 °C(lit.)
Formula C₂₀H₁₈O₈
Boiling Point 626.5 °C at 760 mmHg
Molecular Weight 386.358
Flash Point 223.2 °C
Transport Information
Appearance off-white crystalline powder
Safety 22-24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanedioicacid, 2,3-bis[(4-methylbenzoyl)oxy]-, [R-(R*,R*)]-;(-)-Di-O,O'-p-toluoyltartaric acid;(-)-O,O-Di-p-toluoyltartaric acid;(2R,3R)-(-)-Di(p-toluoyl)tartaric acid;(R,R)-O,O'-Di-p-toluoyltartaric acid;Di-4-toluoyl-L-tartaric acid;L-Di-O,O'-p-toluyltartaric acid;L-Di-p-toluoyltartaric acid;O,O'-Di-p-toluoyl-(2R,3R)-tartaric acid;Tartaricacid, di-p-toluate;
PSA 136.43000
LogP 2.15930

Synthetic route

: 72842-25-2
di-O-p-toluoyl-L-threaric acid-anhydride

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

Conditions

Conditions	Yield
With water

di-O-p-toluoyl-Lg-tartaric acid-anhydride: di-O-p-toluoyl-Lg-tartaric acid-anhydride

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

Conditions

Conditions	Yield
With water; acetone

: 87-69-4
L-Tartaric acid

: 874-60-2
4-methyl-benzoyl chloride

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

Conditions

Conditions	Yield
at 170℃; for 1h;

: 869749-09-7
(R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt

A: 32634-66-5
Di-p-toluoyl-L-tartaric acid

B: 243640-19-9
(2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol

Conditions

Conditions	Yield
Stage #1: (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt With ammonia In methanol; water for 2h; Stage #2: With hydrogenchloride In water Product distribution / selectivity;	A n/a B n/a

: 3-aminomethyl-5-methylhexanoic acid (-)-(O,O')-di-p-toluoyl-L-tartaric acid salt

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

Conditions

Conditions	Yield
In tetrahydrofuran; water at 30℃; for 2.33333 - 3h;

: C10H14N2*C20H18O8

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

Conditions

Conditions	Yield
With hydrogenchloride In tert-butyl methyl ether; water for 0.5h;	345.5 g

: 32634-66-5, 32634-68-7, 100168-11-4, 104528-81-6
rac-O,O'-di-p-toluoyltartaric acid

A: 32634-66-5
Di-p-toluoyl-L-tartaric acid

B: 32634-68-7
(2S,3S)-di-4-toluoyltartaric acid

Conditions

Conditions	Yield
With C22H24N2(2+)*2CF3O3S(1-) In aq. acetate buffer at 20℃; pH=8.1; Resolution of racemate;

: 59729-33-8
1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 1373405-39-0
C20H18O8*C20H21FN2O

Conditions

Conditions	Yield
In isopropyl alcohol Reflux;	100%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol

: 3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol

Conditions

Conditions	Yield
Stage #1: Di-p-toluoyl-L-tartaric acid; 3-amino-1-(5-bromopyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoropropan-2-ol In isopropyl alcohol; acetonitrile at 20 - 50℃; for 1.5h; Stage #2: With potassium carbonate In methanol; water at 20 - 30℃;	99.54%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 103343-47-1
3-amino-5-phenyl-1,3-dihydrobenzo[e][1,4]diazepin-2-one

: C15H13N3O*C20H18O8

Conditions

Conditions	Yield
With air In 1,4-dioxane at 20℃; for 24h;	99%

: 911053-21-9
(R)-1-(1-methyl-but-2-ynyl)-pyrrolidine

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 911053-22-0
(R)-1-(1-methyl-but-2-ynyl)-pyrrolidine di-p-toluoyl-L-tartaric acid salt

Conditions

Conditions	Yield
In dichloromethane	97.4%

: (2SR,3SR)-hydroxybupropion

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

A: 357399-44-1
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol, L-DTTA salt

B: 386210-39-5
C13H18ClNO2*C20H18O8

Conditions

Conditions	Yield
In 2-methylpropyl acetate at 80℃; for 18h; Product distribution / selectivity; Resolution of racemate;	A 97% B n/a
In Isopropyl acetate at 80℃; for 18h; Product distribution / selectivity; Resolution of racemate;	A 92% B n/a
In ethyl acetate at 80℃; for 18h; Product distribution / selectivity; Resolution of racemate;	A 90% B n/a

...Expand

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C12H9F2N

: C12H9F2N*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	97%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 942142-51-0
VTP-27999

: methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate di-p-toluoyl-L-tartrate

Conditions

Conditions	Yield
In ethyl acetate at 50℃; for 0.9h; Product distribution / selectivity;	92%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 54208-72-9
2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol

: C16H25NO3*C20H18O8

Conditions

Conditions	Yield
In methanol	91%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: cis-(+/-)-2-phenylpiperidin-3-ylamine

: C51H48N2O14

Conditions

Conditions	Yield
In methanol at 20 - 60℃; for 3h;	91%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C20H23F2N3O

: C20H23F2N3O*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	91%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: dimethyl 2-(pyridin-3-yl)cyclopropane-1,1-dicarboxylate

: C12H13NO4*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Reagent/catalyst; Solvent; Irradiation;	91%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C16H11NO2

: C16H11NO2*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	91%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 510-77-0, 1668-86-6, 7318-55-0
(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

: [(+)-narwedine]2[di-p-toluoyl-L-tartrate]

Conditions

Conditions	Yield
In ethanol	90%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 510-77-0, 1668-86-6, 7318-55-0
(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

: [(+)-narwedine][di-p-toluoyl-L-tartrate]

Conditions

Conditions	Yield
In ethanol at 20 - 40℃; for 19h; Heating / reflux;	90%

: 5'-chloro-2-(2-pyridinyl)-spiro[cyclopropane-1,3'-[3H]indol]-2'(1'H)-one

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C15H11ClN2O*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	90%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 3-(2,2-difluorocyclopropyl)-6-[5-fluoro-6-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-3-pyridyl]-[1,2,4]triazolo[4,3-b]pyridazine

: C17H13F6N5O*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	90%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 1316216-24-6
(S)-3-amino-1,4,4-trimethylpyrrolidin-2-one

: 1316216-26-8
(S)-3-amino-1,4,4-trimethylpyrrolidin-2-one O,O-di-p-toluoyl-(2R,3R)-tartrate

Conditions

Conditions	Yield
In methanol	89%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 6740-88-1
ketamine

A: (S)-ketamine (-)-O,O'-di-p-toluoyl-L-tartaric acid salt

B: R-(-)-ketamine, (−)-di-p-toluoyl-L-tartaric acid salt

Conditions

Conditions	Yield
In ethanol at 25 - 84℃;	A 89% B 70%

...Expand

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 1-[2-(3-hydroxyadamant-1-yl-amino)acetyl] pyrrolidine-(2S)-carbonitrile

: vildagliptin O,O'-di-p-toluoyl-(2R,3R)-hydrogentartarate

Conditions

Conditions	Yield
Stage #1: 1-[2-(3-hydroxyadamant-1-yl-amino)acetyl] pyrrolidine-(2S)-carbonitrile With hydrogenchloride In ethanol; water Stage #2: Di-p-toluoyl-L-tartaric acid In methanol; ethanol; water at 25 - 50℃; for 3h;	88.8%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 128196-01-0
escitalopram

: 928652-44-2
C20H18O8*C20H21FN2O

Conditions

Conditions	Yield
In ethanol for 2h;	88%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C15H9F5N4O

: C15H9F5N4O*C20H18O8

Conditions

Conditions	Yield
With 2,4,6-triphenylpyrylium tetrafluoroborate In toluene at 20℃; for 3h; Irradiation;	88%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 128196-02-1
(S)-1-[3-(dimethylamino)propyl]-1-(4-flouorphenyl)-1,3-dihydro-5-isobenzofuran carbonitrile

: C20H18O8*C20H21FN2O

Conditions

Conditions	Yield
In ethanol for 2h;	87%

: cis-2-phenyl-3-aminopiperidine

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 168267-14-9, 262598-85-6
[2S]-phenyl-piperidin-[3S]-yl-amine [2R,3R]-bis(4-methyl-benzyloxy)-succinate

Conditions

Conditions	Yield
In ethanol; water at 20℃; Heating;	86%

: (R)-2-amino-2-ethylhexyl hydrogen sulfate

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 69845-06-3
3-hydroxy-4-methoxythiophenol

: (R)-5-((2-amino-2-ethylhexyl)thio)-2-methoxyphenol di-p-toluoyl-L-tartrate

Conditions

Conditions	Yield
Stage #1: (R)-2-amino-2-ethylhexyl hydrogen sulfate With sodium hydroxide In water for 2h; Reflux; Stage #2: 3-hydroxy-4-methoxythiophenol In methanol at 20℃; for 1h; Inert atmosphere; Stage #3: Di-p-toluoyl-L-tartaric acid In acetonitrile at 20 - 45℃; for 7h;	85%

...Expand

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 40571-86-6, 40571-87-7, 51925-39-4, 131164-07-3, 141553-09-5
rac-(1R,2R)-2-(benzylamino)cyclohexanol

A: C33H35NO8

B: 322407-34-1
(1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 65℃; for 3h; optical yield given as %de;	A 83% B n/a

...Expand

: 1025504-45-3
(S)-2-amino-3-methylbutyric acid (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolizin-2-yl ester

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: C20H18O8*C24H38N2O4

Conditions

Conditions	Yield
In dichloromethane; Isopropyl acetate at 45 - 60℃; for 3h;	82%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 151096-09-2
moxifloxacin

: 1082245-36-0
1-cyclopropyl-7-[(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid di-p-toluoyl-L-tartarate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25 - 80℃; for 13 - 16h;	81.93%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 43200-80-2
zopiclon

A: R-zopiclone di-p-toluoyl-L-tartaric acid salt

B: 945843-90-3
eszopiclone di-p-toluoyl-L-tartaric acid salt

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; water at 60 - 65℃; for 1h; Resolution of racemate;	A n/a B 81.5%

...Expand

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 43200-80-2
zopiclon

: 945843-90-3
eszopiclone di-p-toluoyl-L-tartaric acid salt

Conditions

Conditions	Yield
Stage #1: zopiclon In 1-methyl-pyrrolidin-2-one; water at 60 - 65℃; Stage #2: Di-p-toluoyl-L-tartaric acid In 1-methyl-pyrrolidin-2-one; water at 60 - 65℃; for 1h;	81.5%

: 32634-66-5
Di-p-toluoyl-L-tartaric acid

: 1248826-58-5
(S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one

: 1248826-82-5
(S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one mono-(2R,3R)-O,O'-di(p-toluoyl)tartrate

Conditions

Conditions	Yield
In methanol	81%

(-)-Di-p-toluoyl-L-tartaric acid Specification

The CAS registry number of (-)-Di-p-toluoyl-L-tartaric acid is 32634-66-5. Its EINECS registry number is 251-131-7. The IUPAC name is(2R,3R)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid. In addition, the molecular formula is C₂₀H₁₈O₈ and the molecular weight is 386.35. What's more, it is a kind of white to light yellow crystal powder and belongs to the classes of Pharmaceutical Intermediates; Chiral Compounds; Miscellaneous; Carboxylic Acids (Chiral); Chiral Building Blocks; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Hydroxy Acids & Deriv.; Chiral Compound; Inhibitors; Carboxylic Acids Asymmetric Synthesis; Chiral Resolution Reagents; Organic Building Blocks. It should be stored in sealed container, and put in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 6.74; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 1.99; (5)ACD/BCF (pH 5.5): 1.42; (6)ACD/BCF (pH 7.4): 1.39; (7)ACD/KOC (pH 5.5): 2.02; (8)ACD/KOC (pH 7.4): 1.97; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 105.2 Å²; (13)Index of Refraction: 1.596; (14)Molar Refractivity: 95.96 cm³; (15)Molar Volume: 281.6 cm³; (16)Polarizability: 38.04 ×10^-24cm³; (17)Surface Tension: 60.4 dyne/cm; (18)Density: 1.371 g/cm³; (19)Flash Point: 223.2 °C; (20)Enthalpy of Vaporization: 97.48 kJ/mol; (21)Boiling Point: 626.5 °C at 760 mmHg; (22)Vapour Pressure: 1.47E-16 mmHg at 25°C.

Uses of (-)-Di-p-toluoyl-L-tartaric acid: it can react with 2-[(5-Methylimidazol-4-yl)methylthio]-1-propylamine-Dihydrobromid to get C₂₀H₁₈O₈*C₈H₁₅N₃S. This reaction will need reagent NaOEt/EtOH and solvent aq. ethanol. The yield is about 38% with ambient temperature.

(-)-Di-p-toluoyl-L-tartaric acid can react with 2-[(5-Methylimidazol-4-yl)methylthio]-1-propylamine-Dihydrobromid to get C20H18O8*C8H15N3S

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and gloves and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, you should not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccc(cc1)C)C(=O)O)c2ccc(cc2)C
(2)InChI: InChI=1/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t15-,16-/m1/s1
(3)InChIKey: CMIBUZBMZCBCAT-HZPDHXFCBJ

Product Name

(-)-Di-p-toluoyl-L-tartaric acid

Synthetic route

(-)-Di-p-toluoyl-L-tartaric acid Specification

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