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75887-54-6 Usage

Chemical Properties

White Crystalline Solid

Uses

Derivative of Artemisinin. Antimalarial
InChI:InChI=1/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14?,15-,16-,17-/m1/s1

75887-54-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Arteether

1.2 Other means of identification

Product number -
Other names Areether

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:75887-54-6 SDS

75887-54-6Synthetic route

3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide
108739-44-2

3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
chloromethyldimethylsilane In ethanol at 20 - 23℃; for 0.666667 - 1.83333h; Acidic conditions;80.5%
Stage #1: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; chloromethyldimethylsilane In ethanol at 20 - 23℃; for 2h; Acidic conditions;
Stage #2: chloromethyldimethylsilane In ethanol at 20℃; for 2h; Acidic conditions;
74%
Stage #1: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; toluene-4-sulfonic acid In ethanol at 20 - 23℃; for 4h; Acidic conditions;
Stage #2: toluene-4-sulfonic acid In ethanol at 20℃; for 4h; Acidic conditions;
53%
10-ethoxy-9-bromodihydroartemisinin

10-ethoxy-9-bromodihydroartemisinin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); n-Bu3SnH4 In toluene for 20h; Heating;75%
ethanol
64-17-5

ethanol

dihydroartemisinin
71939-50-9

dihydroartemisinin

A

Alpha-Arteether
82534-75-6

Alpha-Arteether

B

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;A n/a
B 72%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

dihydroartesiminin
81496-81-3

dihydroartesiminin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: orthoformic acid triethyl ester; dihydroartesiminin In ethanol at 20℃; for 0.25h;
Stage #2: With acetyl chloride In ethanol at 10 - 15℃;
Stage #3: With sodium hydrogencarbonate In ethanol; water at 0 - 5℃; for 2h;
71.38%
3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide
108739-44-2

3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: artemisin; D-Galactose In ethanol at 20 - 23℃; for 1.58333h;
Stage #2: 3-oxo-8α-hydroxy-6,11β,7αH-eudesm-4-en-6,12-olide; chloromethyldimethylsilane In ethanol for 2h; Acidic conditions;
62%
ethanol
64-17-5

ethanol

dihydroartemisinin
71939-50-9

dihydroartemisinin

A

Alpha-Arteether
82534-75-6

Alpha-Arteether

B

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate
With chloro-trimethyl-silane for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chloro-trimethyl-silane In ethanol at 20 - 23℃; for 1h;
ethanol
64-17-5

ethanol

9,10-dehydrodihydroartemisinin
82596-30-3

9,10-dehydrodihydroartemisinin

A

artemotil
75887-54-6

artemotil

B

11-epi-β-arteether

11-epi-β-arteether

Conditions
ConditionsYield
With triphenylphosphine hydrobromide In dichloromethane for 8h; Ambient temperature; Yield given. Yields of byproduct given;
ethanol
64-17-5

ethanol

dihydroartemisinin
71939-50-9

dihydroartemisinin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 1h; Heating;
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / NaBH4 / methanol / 1 h / 0 °C
2: BF3*Et2O / benzene / 1 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 87 percent / NaBH4
2: 80 percent / P2O5 / CH2Cl2 / 0.5 h / Ambient temperature
3: triphenylphosphine hydrobromide / CH2Cl2 / 8 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 79 percent / sodium borohydride / methanol / 3 h / 0 - 5 °C
2: 72 percent / BF3*Et2O / benzene / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / methanol
2: BF3*OEt2
View Scheme
9,10-dehydrodihydroartemisinin
82596-30-3

9,10-dehydrodihydroartemisinin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. Br2
2: 70 percent / BF3*Et2O / CHCl3 / 10 h / 50 °C
3: 75 percent / n-Bu3SnH4, AIBN / toluene / 20 h / Heating
View Scheme
9-bromodihydroartemisinin

9-bromodihydroartemisinin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / BF3*Et2O / CHCl3 / 10 h / 50 °C
2: 75 percent / n-Bu3SnH4, AIBN / toluene / 20 h / Heating
View Scheme
dihydroartemisinin
71939-50-9

dihydroartemisinin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / P2O5 / CH2Cl2 / 0.5 h / Ambient temperature
2: triphenylphosphine hydrobromide / CH2Cl2 / 8 h / Ambient temperature
View Scheme
dihydroartemisinin
71939-50-9

dihydroartemisinin

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
toluene-4-sulfonic acid In ethanol at 40℃; for 0.25h;
Dowex-50 In ethanol at 30℃; for 10h;
toluene-4-sulfonic acid In ethanol at 20℃; for 0.5h;
aluminum (III) chloride In ethanol at 40℃; for 0.75h; Heating / reflux;
ethanol
64-17-5

ethanol

dihydroartesiminin
81496-81-3

dihydroartesiminin

A

Alpha-Arteether
82534-75-6

Alpha-Arteether

B

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Stage #1: dihydroartesiminin With dodecatungstophosphoric acid hydrate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: ethanol In dichloromethane at 20℃; for 6h; optical yield given as %de;
C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

Alpha-Arteether
82534-75-6

Alpha-Arteether

B

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / methanol
2.1: dodecatungstophosphoric acid hydrate / dichloromethane / 0.08 h / 20 °C
2.2: 6 h / 20 °C
View Scheme
ethanol
64-17-5

ethanol

C12H13O2(CH3)3(O)(OO)
63968-64-9

C12H13O2(CH3)3(O)(OO)

A

Alpha-Arteether
82534-75-6

Alpha-Arteether

B

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With Trimethyl orthoacetate; sodium tetrahydroborate; cellulose sulfuric acid In tetrahydrofuran at -5 - 20℃; for 2.5h; Reagent/catalyst; Overall yield = 82 %;A n/a
B n/a
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

dihydroartesiminin

dihydroartesiminin

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Flow reactor;
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; ethanol / Flow reactor
2: hydrogenchloride / water; ethanol / Flow reactor
View Scheme
dihydroartemisinic acid
85031-59-0, 110715-68-9, 126643-10-5

dihydroartemisinic acid

artemotil
75887-54-6

artemotil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 9,10-Dicyanoanthracene; oxygen / dichloromethane / -20 - 20 °C / UV-irradiation; Flow reactor
1.2: Flow reactor
2.1: lithium chloride; sodium tetrahydroborate / tetrahydrofuran; ethanol / Flow reactor
3.1: hydrogenchloride / water; ethanol / Flow reactor
View Scheme
artemotil
75887-54-6

artemotil

desoxyarteether
112297-79-7

desoxyarteether

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol Ambient temperature;69%
artemotil
75887-54-6

artemotil

9β-hydroxyarteether
130778-40-4

9β-hydroxyarteether

Conditions
ConditionsYield
for 144h; Cunninghamella elegans fermentation;41.7%
artemotil
75887-54-6

artemotil

A

2α-hydroxyarteether

2α-hydroxyarteether

B

14-hydroxyarteether
130778-43-7

14-hydroxyarteether

C

9α-hydroxyarteether
130855-38-8

9α-hydroxyarteether

Conditions
ConditionsYield
Streptomyces lavendulae fermentation;A 32.1%
B 10.7%
C 10.7%
artemotil
75887-54-6

artemotil

1-((2R,3R,3aS,6R,6aS,10aS)-2-Ethoxy-3,6-dimethyl-2,3,3a,4,5,6,6a,7-octahydro-furo[3,2-i]chromen-8-yl)-ethanone

1-((2R,3R,3aS,6R,6aS,10aS)-2-Ethoxy-3,6-dimethyl-2,3,3a,4,5,6,6a,7-octahydro-furo[3,2-i]chromen-8-yl)-ethanone

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 3h; Ambient temperature;7%
artemotil
75887-54-6

artemotil

A

dihydroartemisinin
71939-50-9

dihydroartemisinin

B

Alpha-Arteether
82534-75-6

Alpha-Arteether

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 25℃; Product distribution; var. temp. and β-arteether/FeCl3 ratios;
artemotil
75887-54-6

artemotil

14-hydroxyarteether β-glucuronide

14-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 36.23 mg / silver carbonate / benzene / 72 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
artemotil
75887-54-6

artemotil

2α-hydroxyarteether β-glucuronide

2α-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 32.1 percent / Streptomyces lavendulae fermentation
2: 19.75 mg / silver carbonate / benzene / 240 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: silver carbonate / benzene / 72 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15
163562-60-5

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32.1 percent / Streptomyces lavendulae fermentation
2: 19.75 mg / silver carbonate / benzene / 240 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 36.23 mg / silver carbonate / benzene / 72 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

9β-hydroxyarteether β-glucuronide

9β-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: 10.35 mg / silver carbonate / benzene / 192 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
artemotil
75887-54-6

artemotil

9α-hydroxyarteether β-glucuronide

9α-hydroxyarteether β-glucuronide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 15.67 mg / silver carbonate / benzene / 336 h / Ambient temperature
3: 5 N KOH / methanol / 2.5 h
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: silver carbonate / benzene / 192 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: silver carbonate / benzene / 336 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41.7 percent / 144 h / Cunninghamella elegans fermentation
2: 10.35 mg / silver carbonate / benzene / 192 h / Ambient temperature
View Scheme
artemotil
75887-54-6

artemotil

C30H44O15

C30H44O15

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10.7 percent / Streptomyces lavendulae fermentation
2: 15.67 mg / silver carbonate / benzene / 336 h / Ambient temperature
View Scheme

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