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(-)-Diethyl D-tartrate

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Name

(-)-Diethyl D-tartrate

EINECS 237-458-8
CAS No. 13811-71-7 Density 1.262 g/cm3
PSA 93.06000 LogP -1.16560
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 N/A 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;

Article Data 16

(-)-Diethyl D-tartrate Synthetic route

64-17-5

ethanol

147-71-7

D-tartaric acid

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

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

13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With indium; water; ammonium chloride In methanol for 2h; Heating;85%
136087-36-0

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

13811-71-7

diethyl (2S,3S)-tartrate

Conditions
ConditionsYield
With sodium azide In ethanol; water at 20℃; for 14h;
136087-36-0

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

A

13811-71-7

diethyl (2S,3S)-tartrate

B

101924-53-2

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

C

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

Conditions
ConditionsYield
With sodium azide In water; N,N-dimethyl-formamide at 20℃; for 14h;
57968-71-5

(+/-)-diethyl tartrate

A

13811-71-7

diethyl (2S,3S)-tartrate

B

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
13811-71-7

diethyl (2S,3S)-tartrate

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%
109-87-5

Dimethoxymethane

13811-71-7

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

diethyl (2S,3S)-tartrate

1034-39-5

dibromotriphenylphosphorane

(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%
13811-71-7

diethyl (2S,3S)-tartrate

77-78-1

dimethyl sulfate

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%

(-)-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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