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13811-71-7

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13811-71-7 Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Diethyl D(-)-tartrate is mainly used in chiral pharmaceuticals, chiral intermediates and chiral catalysts. It can be used with titanium in enolic asymmetric epoxidization. The compound d-alpha-tocopherol is the principal compound present in natural vitamin E sources. At present, d-alpha-tocopherol and other tocopherol derivatives are used in pharmaceuticals, foods and animal feeds. It is used as a food additive.

Purification Methods

Distil the esters under high vacuum and store them under vacuum or in an inert atmosphere in a desiccator in round bottomed flasks equiped with a vacuum stopcock. They have also been distilled by Kügelrohr distillation and/or by 'wiped-film' molecular distillation. They are slightly soluble in H2O but miscible with EtOH and Et2O. [Gao et al. J Am Chem Soc 109 5770 (5771) 1987, IR: Pristera Anal Chem 25 844 1953, Beilstein 3 III 1025 for D-(-), 3 IV 1232 for L(+).]

Check Digit Verification of cas no

The CAS Registry Mumber 13811-71-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,8,1 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13811-71:
(7*1)+(6*3)+(5*8)+(4*1)+(3*1)+(2*7)+(1*1)=87
87 % 10 = 7
So 13811-71-7 is a valid CAS Registry Number.
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

13811-71-7 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (T1195)  Diethyl D-(-)-Tartrate  >97.0%(GC)

  • 13811-71-7

  • 25g

  • 350.00CNY

  • Detail
  • TCI America

  • (T1195)  Diethyl D-(-)-Tartrate  >97.0%(GC)

  • 13811-71-7

  • 250g

  • 2,000.00CNY

  • Detail
  • Alfa Aesar

  • (A17992)  (-)-Diethyl D-tartrate, 99%   

  • 13811-71-7

  • 5g

  • 256.0CNY

  • Detail
  • Alfa Aesar

  • (A17992)  (-)-Diethyl D-tartrate, 99%   

  • 13811-71-7

  • 25g

  • 804.0CNY

  • Detail
  • Alfa Aesar

  • (A17992)  (-)-Diethyl D-tartrate, 99%   

  • 13811-71-7

  • 100g

  • 2767.0CNY

  • Detail
  • Aldrich

  • (213969)  (−)-DiethylD-tartrate  ≥99%

  • 13811-71-7

  • 213969-5G

  • 276.12CNY

  • Detail
  • Aldrich

  • (213969)  (−)-DiethylD-tartrate  ≥99%

  • 13811-71-7

  • 213969-25G

  • 851.76CNY

  • Detail
  • Aldrich

  • (213969)  (−)-DiethylD-tartrate  ≥99%

  • 13811-71-7

  • 213969-500G

  • 10,389.60CNY

  • Detail

13811-71-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-Diethyl D-tartrate

1.2 Other means of identification

Product number -
Other names Diethyl D-(-)-tartrate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13811-71-7 SDS

13811-71-7Synthetic 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;
(+/-)-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%
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%
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%
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%

13811-71-7Relevant articles and documents

Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents

Li, Bing,Wang, Kaiyuan,Zhang, Rui,Li, Baihui,Shen, Yangli,Ji, Qinggang

supporting information, (2019/09/07)

A series of 2,8-diazaspiro[4.5]decan-1-one derivatives were designed, synthesized and screened for their inhibition activities against chitin synthase (CHS) and antimicrobial activities in vitro. The biological assays revealed that compounds 4a, 4e, 4h, 4j, 4o, 4q and 4r exhibited moderated to excellent potency against CHS with IC50 values ranging from 0.12 to 0.29 mM. Compounds 4e, 4j with IC50 value of 0.13 mM, 0.12 mM respectively, showed excellent inhibition potency among these compounds, which were similar to that of polyoxin B whose IC50 value was 0.08 mM. Meanwhile, the screening of the antifungal activity showed that compounds 4j and 4r had the same potency of inhibiting the growth of A. fumigatus with MIC value of 0.08 mmol/L. Compound 4d displayed excellent activity against C. albicans (ATCC 90023) with MIC value of 0.04 mmol/L, which was superior to fluconazole (0.104 mmol/L) and polyoxin B (0.129 mmol/L). The result of antibacterial assay showed that these compounds had little potency against those selected bacteria strains including three Gram-positive bacteria and three Gram-negative bacteria. Furthermore, the combination use of 4c-fluconazole, 4i-fluconazole, 4j-fluconazole, and 4o-fluconazole against C. albicans,A. fumigatus and A. flavus showed additive or synergistic effects. These results indicated that the designed compounds serve as potential chitin synthase inhibitors and have selectively antifungal activities.

High-purity manufacturing method of dialkyl tartrate

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Paragraph 0165-0170, (2017/03/24)

The invention provides an efficient method for manufacturing high purity tartaric acid dialkyl esters, including the steps of: reacting fatty alcohol of alkyl with 1-4 carbon atom(s) with tartaric acid without solvents and acid catalysts, and then performing concentration until moisture content becomes below 1.0 weight% to obtain a first esterification reaction liquid; adding fatty alcohol of a same kind into the first esterification reaction liquid to prepare a homogeneous solution, and then adding thionyl chloride for reaction to perform concentration to obtain a second esterification reaction liquid; adding solid shaped bicarbonate into the second esterification reaction liquid for neutralization, and performing solid-liquid separation, concentration and thin-film distillation. According to the method, high purity tartaric acid dialkyl esters with the content of sulfurous acid dialkyl esters below 0.1% and content of tartaric acid monoalkyl esters below 0.1% is obtained.

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Zeng, Jing,Zhang, Qian,Zhang, Hong-Kui,Chen, Anqi

, p. 20298 - 20307 (2013/11/06)

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.

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