Product Name

  • Name

    (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester

  • EINECS 237-458-8
  • CAS No. 13811-71-7
  • Article Data16
  • CAS DataBase
  • Density 1.262 g/cm3
  • Solubility insoluble in water
  • Melting Point 17 °C
  • Formula C8H14O6
  • Boiling Point 280 °C at 760 mmHg
  • Molecular Weight 206.196
  • Flash Point 93.3 °C
  • Transport Information
  • Appearance Colorless to light yellow liquid
  • Safety 24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 13811-71-7 ((2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester)
  • Hazard Symbols IrritantXiIrritantXi
  • Synonyms Butanedioicacid, 2,3-dihydroxy-, diethyl ester, [S-(R*,R*)]- (9CI);Tartaric acid, diethylester, (-)- (8CI);(2S,3S)-Diethyl tartrate;(S,S)-Diethyl tartrate;D-(-)-Diethyl tartrate;D-Tartaric acid diethyl ester;Diethyl (-)-D-tartrate;Diethyl (2S,3S)-(-)-tartrate;Diethyl(S,S)-(-)-tartrate;
  • PSA 93.06000
  • LogP -1.16560

Synthetic route

ethanol
64-17-5

ethanol

D-tartaric acid
147-71-7

D-tartaric acid

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With thionyl chloride at 20℃;100%
With thionyl chloride at 20℃;100%
With hydrogenchloride In chloroform; water for 60h; Catalytic behavior; Reflux; enantioselective reaction;99.6%
(2S,3S)-2,3-Bis-(2,2,2-trichloro-acetoxy)-succinic acid diethyl ester

(2S,3S)-2,3-Bis-(2,2,2-trichloro-acetoxy)-succinic acid diethyl ester

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With indium; water; ammonium chloride In methanol for 1h; Heating;89%
(2S,3S)-2,3-Bis-(2,2,2-trichloro-ethoxycarbonyloxy)-succinic acid diethyl ester

(2S,3S)-2,3-Bis-(2,2,2-trichloro-ethoxycarbonyloxy)-succinic acid diethyl ester

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With indium; water; ammonium chloride In methanol for 2h; Heating;85%
diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide
136087-36-0

diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With sodium azide In ethanol; water at 20℃; for 14h;
diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide
136087-36-0

diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide

A

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

B

diethyl (2S,3R)-2-azido-3-hydroxysuccinate
101924-53-2

diethyl (2S,3R)-2-azido-3-hydroxysuccinate

C

diethyl (2R,3R)-2-azido-3-hydroxysuccinate

diethyl (2R,3R)-2-azido-3-hydroxysuccinate

Conditions
ConditionsYield
With sodium azide In water; N,N-dimethyl-formamide at 20℃; for 14h;
...Expand
(+/-)-diethyl tartrate
57968-71-5

(+/-)-diethyl tartrate

A

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

B

diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

Conditions
ConditionsYield
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
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

diethyl (4S,5S)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide
35506-91-3, 133522-25-5, 136087-36-0

diethyl (4S,5S)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide

Conditions
ConditionsYield
With thionyl chloride In tetrachloromethane Heating;100%
With thionyl chloride; triethylamine In dichloromethane for 3h;100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 50℃; for 2.5h;95%
Dimethoxymethane
109-87-5

Dimethoxymethane

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate
159593-22-3

diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate

Conditions
ConditionsYield
With phosphorus pentoxide In dichloromethane100%
With phosphorus pentoxide In dichloromethane for 3h;100%
With phosphorus pentoxide In chloroform for 2h; Alkylation;84%
With phosphorus pentoxide In dichloromethane
With phosphorus pentoxide In dichloromethane at 0℃; for 10h; Inert atmosphere;
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

dibromotriphenylphosphorane
1034-39-5

dibromotriphenylphosphorane

(4S,5S)-2,2,2-Triphenyl-2λ5-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid diethyl ester

(4S,5S)-2,2,2-Triphenyl-2λ5-[1,3,2]dioxaphospholane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In toluene Cyclization;100%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

dimethyl sulfate
77-78-1

dimethyl sulfate

(-)-(2S,3S)-O,O-Dimethylweinsaeure-diethylester
21066-69-3

(-)-(2S,3S)-O,O-Dimethylweinsaeure-diethylester

Conditions
ConditionsYield
With sodium hydride In diethyl ether at 0 - 20℃; Inert atmosphere;100%
With sodium hydride In mineral oil at 0 - 20℃; for 12h;82%
titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

omeprazole sodium

omeprazole sodium

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

3C8H8O3*C8H14O6*C12H28O4Ti*C17H19N3O3S

3C8H8O3*C8H14O6*C12H28O4Ti*C17H19N3O3S

Conditions
ConditionsYield
Stage #1: titanium(IV) isopropylate; omeprazole sodium; diethyl (2S,3S)-tartrate With triethylamine In propan-1-ol at 40℃; for 0.166667h;
Stage #2: (S)-Mandelic acid In propan-1-ol at 40℃; for 3h; Product distribution / selectivity;		99.8%
...Expand
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

diethyl (2S,3R)-(+)-erythro-2-hydroxy-3-bromosuccinate
80640-15-9

diethyl (2S,3R)-(+)-erythro-2-hydroxy-3-bromosuccinate

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 0 - 25℃; for 13h; Inert atmosphere;99.1%
With hydrogen bromide; acetic acid at 0 - 20℃; for 12h;99.1%
With hydrogen bromide; acetic acid In benzene Heating;90%
Stage #1: diethyl (2S,3S)-tartrate With hydrogen bromide; acetic acid at 20℃; for 16h;
Stage #2: With ethanol; acetyl chloride for 5h; Heating;
Multi-step reaction with 2 steps
1: hydrogen bromide / 6.25 h / 0 - 20 °C
2: hydrogen bromide / acetic acid; ethanol / 10 h / Reflux
View Scheme
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

(2S,3S)-2,3-O-(4-methoxybenzylidene)-diethyl tartrate
135972-13-3

(2S,3S)-2,3-O-(4-methoxybenzylidene)-diethyl tartrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 10 Torr; for 5h;99%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 18 Torr; for 5h;99%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide96%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

acetone
67-64-1

acetone

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
73346-73-3

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With orthoformic acid triethyl ester99%
With iodine at 20℃; for 12h;77%
In orthoformic acid triethyl ester at 20℃; Reflux;72.6 g
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

C15H17O2Pol

C15H17O2Pol

C25H35O8Pol

C25H35O8Pol

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate at 0 - 20℃; solid phase reaction;99%
...Expand
methoxyethene
107-25-5

methoxyethene

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

(2S,3S)-2,3-bis(1'-methoxyaethoxy)-bernsteinsaeurediaethylester

(2S,3S)-2,3-bis(1'-methoxyaethoxy)-bernsteinsaeurediaethylester

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 48h; 0 deg C then room temp.;98%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 45℃; for 9h; Temperature; Reagent/catalyst; Reflux;98%
With camphor-10-sulfonic acid68.5%
With toluene-4-sulfonic acid; triethylamine In chloroform for 17h; Reflux;48.8%
With toluene-4-sulfonic acid In chloroform for 18h; Reflux;42.8%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

benzyl bromide
100-39-0

benzyl bromide

(2S,3S)-diethyl 2,3-bis(phenylmethoxy)succinate
113321-58-7

(2S,3S)-diethyl 2,3-bis(phenylmethoxy)succinate

Conditions
ConditionsYield
With potassium iodide; silver(l) oxide In dichloromethane for 1h; Heating;97%
With potassium iodide; silver(l) oxide In dichloromethane for 1h; Reflux; Inert atmosphere;97%
With thallium (I) ethoxide In acetonitrile 1.) 55 deg C, 48 h, 2.) room temp., 12 h;88%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
73346-73-3

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
Acidic conditions;97%
With toluene-4-sulfonic acid In dichloromethane at 40℃; for 17h;90%
With toluene-4-sulfonic acid In benzene for 8h; Reflux;79.2%
3,3-dimethoxypentane
25636-49-1

3,3-dimethoxypentane

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate
1226768-08-6

diethyl (4S,5S)-2,2-diethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 3h; Inert atmosphere; Reflux;96%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

D-(S,S)-2-ethoxy-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester
95588-28-6

D-(S,S)-2-ethoxy-1,3-dioxolane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With camphor-10-sulfonic acid In toluene at 95℃;95%
With acetic acid In toluene Heating;94%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

benzaldehyde
100-52-7

benzaldehyde

diethyl(4S,5S)-2-phenyl-1,3-dioxolan-4,5-dicarboxylate
141042-56-0

diethyl(4S,5S)-2-phenyl-1,3-dioxolan-4,5-dicarboxylate

Conditions
ConditionsYield
Stage #1: benzaldehyde With camphor-10-sulfonic acid; toluene-4-sulfonic acid; orthoformic acid triethyl ester In toluene for 0.75h; Heating / reflux;
Stage #2: diethyl (2S,3S)-tartrate In toluene Heating / reflux;		94.1%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester84%
With toluene-4-sulfonic acid In cyclohexane for 4h; Reflux;
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

benzylamine
100-46-9

benzylamine

N,N'-dibenzyl-(S,S)-tartaric acid diamide
108321-43-3

N,N'-dibenzyl-(S,S)-tartaric acid diamide

Conditions
ConditionsYield
With potassium carbonate In methanol for 8h; Heating;94%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

diethyl (2S,3R)-erythro-2-acetoxy-3-bromosuccinate
74213-59-5

diethyl (2S,3R)-erythro-2-acetoxy-3-bromosuccinate

Conditions
ConditionsYield
With hydrogen bromide In acetic acid for 4h; Ambient temperature;93%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

benzyl bromide
100-39-0

benzyl bromide

diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate
119770-87-5

diethyl (2S,3S)-2-(benzyloxy)-3-hydroxybutanedioate

Conditions
ConditionsYield
With tetrabutylammomium bromide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine In neat (no solvent) at 70℃; for 1h; regioselective reaction;93%
With silver(l) oxide In dichloromethane at 20℃; for 2h;17.9 g
ethanol-toluene

ethanol-toluene

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

(E)-α-hexylcinnamaldehyde
165184-98-5

(E)-α-hexylcinnamaldehyde

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

(E)-(4R,5R)-2-(1-Hexyl-2-phenyl-1-ethenyl)-4,5-dicarboethoxy-1,3-dioxolane
144407-12-5

(E)-(4R,5R)-2-(1-Hexyl-2-phenyl-1-ethenyl)-4,5-dicarboethoxy-1,3-dioxolane

Conditions
ConditionsYield
In toluene-4-sulfonic acid; toluene91%
...Expand
pyrrolidine
123-75-1

pyrrolidine

diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

1,1'-[(2R,3R)-2,3-dihydroxy-1,4-dioxo-1,4-butanediyl]bis-pyrrolidine
102197-56-8

1,1'-[(2R,3R)-2,3-dihydroxy-1,4-dioxo-1,4-butanediyl]bis-pyrrolidine

Conditions
ConditionsYield
In ethanol for 12h; Reflux;91%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

(4S,5S)-2-oxo[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

(4S,5S)-2-oxo[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With pyrographite In tetrahydrofuran at 50℃; for 120h;90%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

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

diethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide

Conditions
ConditionsYield
With pyridine; thionyl chloride In dichloromethane at 0℃;90%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

acetone
67-64-1

acetone

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
59779-75-8

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In N,N-dimethyl-formamide for 72h; Ambient temperature;89.5%
With toluene-4-sulfonic acid In toluene for 15h; Inert atmosphere; Reflux;18%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

cyclopentanone
120-92-3

cyclopentanone

(2S,3S)-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid diethyl ester

(2S,3S)-1,4-dioxa-spiro[4.4]nonane-2,3-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 36h; Heating;88%
With 10-camphorsulfonic acid In toluene at 150℃; for 24h;
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

chloroacetyl chloride
79-04-9

chloroacetyl chloride

(2S,3S)-2,3-Bis-(2-chloro-acetoxy)-succinic acid diethyl ester
226710-54-9

(2S,3S)-2,3-Bis-(2-chloro-acetoxy)-succinic acid diethyl ester

Conditions
ConditionsYield
With pyridine In chloroform for 5h; Ambient temperature;87.3%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

4-(Phenylsulfonyl)-2-butanon-dimethylacetal
85785-78-0

4-(Phenylsulfonyl)-2-butanon-dimethylacetal

(4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester
85785-79-1

(4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 80 - 90℃; for 20h;87%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

benzaldehyde
100-52-7

benzaldehyde

diethyl-2,3-O-benzylidene-D-tartrate
21154-16-5, 35572-31-7, 89015-57-6, 141042-56-0

diethyl-2,3-O-benzylidene-D-tartrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In cyclohexane for 16h; Catalytic behavior; Reflux; enantioselective reaction;87%

(-)-Diethyl D-tartrate Chemical Properties

Name : (-)-Diethyl D-tartrate
Synonyms : (-)-Diethyl-2,3-dihydroxysuccinate; (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
 
Molecular Structure :        
 
Molecular Formula : C8H14O6
Molecular Weight : 206.19
CAS Registry Number : 13811-71-7
EINECS : 237-458-8
Melting point : 17 oC
Boiling point : 280 oC
Flash point : 93 oC
Density : 1.205
Refractive index : 1.445-1.447 
Water solubility : insoluble

(-)-Diethyl D-tartrate Safety Profile

(-)-Diethyl D-tartrate avoid contact with skin or eyes

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