CAS No.505-75-9,cicutoxin Suppliers

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8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(8E,10E,12E,14R)- cas 505-75-9Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express

8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(8E,10E,12E,14R)- cas 505-75-9

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Shanghai united Scientific Co.,Ltd.

United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat

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Nanjing Raymon Biotech Co., Ltd.

8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(8E,10E,12E,14R)-Appearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/Pharmaceutical intermediates

8,10,12-Heptadecatriene-4,6-diyne-1,14-diol,(8E,10E,12E,14R)-

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Synthetic route

: 1150616-77-5
(4R,5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h; Inert atmosphere;	61%
With toluene-4-sulfonic acid In methanol at 20℃; for 1.5h; Darkness;	53%

: 1001587-76-3
7-bromohepta-4,6-diyn-1-ol

: 1265526-17-7
(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium fluoride; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol In 1-methyl-pyrrolidin-2-one at 45℃; for 3.5h; Stille coupling; Inert atmosphere;

: 1265526-19-9
7-iodohepta-4,6-diyn-1-ol

: 1265526-17-7
(4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran at 20 - 45℃; for 5h; Stille coupling; Inert atmosphere;

: 5390-04-5
pent-1-yn-5-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: iodine; potassium hydroxide / methanol; water / 7 h / 20 °C 2: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent) 3: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 4: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1: iodine; potassium hydroxide / methanol; water / 7 h / 20 °C
2: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent)
3: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness
4: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere
View Scheme

: 83670-22-8
7-(trimethylsilyl)hepta-4,6-diyn-1-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 2: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme

: 94230-39-4
5-iodo-4-pentyn-1-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent) 2: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness 3: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 3 steps
1: piperidine; copper(l) chloride / 1 h / 0 °C / Inert atmosphere; Neat (no solvent)
2: N-Bromosuccinimide; silver nitrate / acetone / 18 h / 20 °C / Inert atmosphere; Darkness
3: copper(l) iodide; potassium fluoride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / 1-methyl-pyrrolidin-2-one / 3.5 h / 45 °C / Inert atmosphere
View Scheme

: 646534-13-6
(E)-7-chlorohept-6-en-4-yn-1-ol

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 2.1: copper(l) iodide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol / tetrahydrofuran / 5 h / 20 - 45 °C / Inert atmosphere View Scheme

: (5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐one

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 2: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

: C17H20O4

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 12 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique 2.2: 12 h 3.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique 4.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 5.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 6.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 12 h / 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique
2.2: 12 h
3.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
4.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
5.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
6.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme

: C17H20O3

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 2: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 3: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

: 159646-46-5
2‐(hepta‐4,6‐diyn‐1‐yloxy)tetrahydro‐2H‐pyran

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: methyllithium / tetrahydrofuran; diethyl ether / 0.5 h / Schlenk technique 1.2: 1 h / -78 °C 1.3: 4 h / -78 - 20 °C 2.1: 12 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique 3.2: 12 h 4.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique 5.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 6.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 7.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

Yield

Multi-step reaction with 7 steps
1.1: methyllithium / tetrahydrofuran; diethyl ether / 0.5 h / Schlenk technique
1.2: 1 h / -78 °C
1.3: 4 h / -78 - 20 °C
2.1: 12 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique
3.2: 12 h
4.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
5.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
6.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
7.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme

: (2E,4E)‐12‐((tetrahydro‐2H‐pyran‐2‐yl) oxy)dodeca‐2,4‐dien‐6,8‐diynoic acid

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique 1.2: 12 h 2.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique 3.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 4.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 5.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / 20 °C / Schlenk technique
1.2: 12 h
2.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
3.1: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
4.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
5.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme

: (2E,4E)‐N‐methoxy‐N‐methyl‐12-((tetrahydro‐2H‐pyran‐2‐yl)oxy)dodeca‐2,4‐dien‐6,8‐diyne amide

: 505-75-9
Cicutotoxin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique 2: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness 3: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C 4: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness View Scheme

Yield

Multi-step reaction with 4 steps
1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 °C / Darkness; Schlenk technique
2: barium(II) hydroxide / tetrahydrofuran; water / 0.5 h / 20 °C / Schlenk technique; Darkness
3: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1.5 h / -50 °C
4: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Darkness
View Scheme

: 18162-48-6
tert-butyldimethylsilyl chloride

: 505-75-9
Cicutotoxin

: (5E,7E,9E)-(R)-17-(tert-Butyl-dimethyl-silanyloxy)-heptadeca-5,7,9-triene-11,13-diyn-4-ol

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃; for 3h; Substitution;	80%

: 39637-99-5, 20445-33-4
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

: 505-75-9
Cicutotoxin

: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Esterification;	76%

: 108-24-7
acetic anhydride

: 505-75-9
Cicutotoxin

A: Acetic acid (8E,10E,12E)-(R)-14-hydroxy-heptadeca-8,10,12-triene-4,6-diynyl ester

B: Acetic acid (2E,4E,6E)-(R)-14-acetoxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

C: Acetic acid (2E,4E,6E)-(R)-14-hydroxy-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions

Conditions	Yield
With pyridine at 0℃; for 8.3h;	A 55% B 23% C 10%

...Expand

: 505-75-9
Cicutotoxin

: 74-88-4
methyl iodide

A: (8E,10E,12E)-(R)-1,14-Dimethoxy-heptadeca-8,10,12-triene-4,6-diyne

B: (14R)-(8E,10E,12E)-14-methoxyheptadecatriene-4,6-diyn-1-ol

C: (5E,7E,9E)-(R)-17-Methoxy-heptadeca-5,7,9-triene-11,13-diyn-4-ol

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.166667h;	A 27% B 5% C 24%

...Expand

: 505-75-9
Cicutotoxin

A: 25525-18-2
17-hydroxy-heptadeca-5t,7t,9t-triene-11,13-diyn-4-one

B: (8E,10E,12E)-14-oxoheptadecatriene-4,6-diyn-1-al

C: 321655-32-7
(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynal

Conditions

Conditions	Yield
With pyridine-SO3 complex; dimethyl sulfoxide; triethylamine In dichloromethane at 0℃; for 4h;	A 8% B 16% C 13%

...Expand

: 20445-33-4, 39637-99-5
(R)-methoxytrifluoromethylphenylacetyl chloride

: 505-75-9
Cicutotoxin

: (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2E,4E,6E)-(R)-1-propyl-14-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Esterification;

: 505-75-9
Cicutotoxin

: 321655-37-2
(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C 2: 71 percent / KOH; I2 / 0.25 h / 0 °C 3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C View Scheme

: 505-75-9
Cicutotoxin

: 321655-36-1
(8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C 2: 71 percent / KOH; I2 / 0.25 h / 0 °C View Scheme

: 505-75-9
Cicutotoxin

: (8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid amide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C 2: 71 percent / KOH; I2 / 0.25 h / 0 °C 3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C 4: 63 percent / NH4Cl; DPPA; Et3N / dimethylformamide / 8.5 h / 0 °C View Scheme

: 505-75-9
Cicutotoxin

: (8E,10E,12E)-(R)-14-Hydroxy-heptadeca-8,10,12-triene-4,6-diynoic acid butylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 13 percent / DMSO; SO3*pyridine; Et3N / CH2Cl2 / 4 h / 0 °C 2: 71 percent / KOH; I2 / 0.25 h / 0 °C 3: 75 percent / 1 N aq. NaOH / methanol / 9 h / 20 °C 4: 70 percent / DPPA; Et3N / dimethylformamide / 9.5 h / 0 °C View Scheme

: 505-75-9
Cicutotoxin

: 4-Methoxy-benzoic acid (2E,4E,6E)-(R)-14-(tert-butyl-dimethyl-silanyloxy)-1-propyl-tetradeca-2,4,6-triene-8,10-diynyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / Et3N, DMAP / CH2Cl2 / 3 h / 0 °C 2: 94 percent / Et3N, DMAP / CH2Cl2 / 3 h / 0 °C View Scheme

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