Product Name

  • Name

    Largazole

  • EINECS
  • CAS No. 1009815-87-5
  • Article Data18
  • CAS DataBase
  • Density 1.317 g/cm3
  • Solubility
  • Melting Point
  • Formula C29H42N4O5S3
  • Boiling Point
  • Molecular Weight 622.874
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 1009815-87-5 (Largazole)
  • Hazard Symbols
  • Synonyms Largazole
  • PSA 212.64000
  • LogP 5.02170

Synthetic route

Largazole thiol
1033814-08-2

Largazole thiol

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;94%
With triethylamine In dichloromethane at 0 - 20℃;94%
Stage #1: Largazole thiol With chlorotriisopropylsilane; triethylamine; trifluoroacetic acid In dichloromethane
Stage #2: n-octanoic acid chloride With triethylamine In dichloromethane at 20℃; for 2h;		94%
C58H64N4O8S3
1263375-82-1

C58H64N4O8S3

A

largazole
1009815-87-5

largazole

B

2-epi-largazole
1196806-45-7

2-epi-largazole

Conditions
ConditionsYield
Stage #1: C58H64N4O8S3 With diethylamine In dichloromethane at 20 - 25℃; for 3h; Inert atmosphere;
Stage #2: With 1-hydroxy-7-azabenzotriazole; N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20 - 25℃; for 12h; Inert atmosphere;		A 29%
B 43%
Multi-step reaction with 2 steps
1.1: diethylamine / dichloromethane / 3 h / 20 - 25 °C
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 - 25 °C
2.2: 12 h / 20 - 25 °C
View Scheme
octanethioic S-acid
7530-92-9

octanethioic S-acid

(5R,8S,11S)-11-((E)-4-chlorobut-1-en-1-yl)-8-isopropyl-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione

(5R,8S,11S)-11-((E)-4-chlorobut-1-en-1-yl)-8-isopropyl-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 25℃; for 16h; Inert atmosphere;42%
S-but-3-enyl octanethionate
1033813-95-4

S-but-3-enyl octanethionate

C19H24N4O4S2
1033813-96-5

C19H24N4O4S2

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 110℃; for 4h;41%
Stage #1: S-but-3-enyl octanethionate; C19H24N4O4S2; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 110℃; for 4h;
Stage #2: With dimethyl sulfoxide In toluene at 20℃;		41%
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 60℃; for 24h; Inert atmosphere;34%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 90℃; Inert atmosphere; Sealed tube;27%
S-but-3-enyl octanethionate
1033813-95-4

S-but-3-enyl octanethionate

C19H24N4O4S2
1033813-96-5

C19H24N4O4S2

A

largazole
1009815-87-5

largazole

B

largazole

largazole

Conditions
ConditionsYield
With 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)dichloro(5-nitro-2-isopropoxyphenylmethylene)ruthenium In 1,2-dichloro-ethane at 90℃; for 12h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
...Expand
C29H44N4O6S3

C29H44N4O6S3

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
With HOAt; 2-(1H-benzotriazole-1-yL)-1,1,3,3-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 4h;6.3 mg
C29H44N4O6S3

C29H44N4O6S3

A

largazole
1009815-87-5

largazole

B

largazole

largazole

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 48h;A 20 mg
B 2 mg
C43H54N4O6S3

C43H54N4O6S3

A

largazole
1009815-87-5

largazole

B

2-epi-largazole
1196806-45-7

2-epi-largazole

Conditions
ConditionsYield
Stage #1: C43H54N4O6S3 With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 25℃; for 0.166667h;
Stage #2: With 1-hydroxy-7-aza-benzotriazole; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 25℃; for 12h;		A 1.2 mg
B 1.8 mg
methyl 2-(tert-butoxycarbonylaminomethyl)thiazole-4-carboxylate
297165-32-3

methyl 2-(tert-butoxycarbonylaminomethyl)thiazole-4-carboxylate

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: lithium hydroxide / tetrahydrofuran; water / 0 - 20 °C
1.2: pH 1 - 2
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 0.17 h
3.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C
4.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / aq. phosphate buffer
5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
5.2: 0 - 20 °C
6.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
7.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
8.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
9.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
(R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid
1033814-13-9

(R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
1.2: 0 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
3.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
4.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: hydrogenchloride / 0.08 h
2.1: dmap / dichloromethane / 0.08 h
2.2: 1 h
3.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
3.2: 0 - 20 °C
4.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
5.1: diethylamine / dichloromethane / 3 h / 20 °C
6.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
7.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
8.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-amino-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate
1137735-74-0

(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-amino-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
1.2: 0 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
3.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
4.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate
1043577-34-9

(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
2: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
3: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
4: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
C40H44N4O5S3

C40H44N4O5S3

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
2: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
3: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
(5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione
1043577-37-2

(5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-triene-6,9,13-trione

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: dichloromethane / 2 h / 20 °C
2.1: trifluoroacetic acid; chlorotriisopropylsilane; triethylamine / dichloromethane
2.2: 2 h / 20 °C
View Scheme
C51H57NO5SSi

C51H57NO5SSi

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: diethylamine / acetonitrile / 2 h
2.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
2.2: 0 - 20 °C
3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
4.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
5.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid
71904-80-8

2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 0.17 h
2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C
3.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / aq. phosphate buffer
4.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
4.2: 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
6.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
7.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
8.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C
1.2: 2 h / 20 °C
2.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1 h / 0 - 20 °C
3.1: sodium hydrogencarbonate / methanol / 1 h / 70 °C / pH 5.95 / Inert atmosphere; phosphate buffer
4.1: hydrogenchloride / 0.08 h
5.1: dmap / dichloromethane / 0.08 h
5.2: 1 h
6.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
6.2: 0 - 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
8.1: diethylamine / dichloromethane / 3 h / 20 °C
9.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
10.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
11.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide
182120-82-7

2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C
2.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / aq. phosphate buffer
3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
3.2: 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
5.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
6.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1 h / 0 - 20 °C
2.1: sodium hydrogencarbonate / methanol / 1 h / 70 °C / pH 5.95 / Inert atmosphere; phosphate buffer
3.1: hydrogenchloride / 0.08 h
4.1: dmap / dichloromethane / 0.08 h
4.2: 1 h
5.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
5.2: 0 - 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
7.1: diethylamine / dichloromethane / 3 h / 20 °C
8.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
9.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
10.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile
251294-64-1

2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / aq. phosphate buffer
2.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
2.2: 0 - 20 °C
3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
4.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane; acetonitrile
5.1: triethylsilane; trifluoroacetic anhydride / 2 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium hydrogencarbonate / methanol / 1 h / 70 °C / pH 5.95 / Inert atmosphere; phosphate buffer
2.1: hydrogenchloride / 0.08 h
3.1: dmap / dichloromethane / 0.08 h
3.2: 1 h
4.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
4.2: 0 - 20 °C
5.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
6.1: diethylamine / dichloromethane / 3 h / 20 °C
7.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
8.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
9.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: triethylamine / 72 h / 50 °C
2.1: dichloromethane / 1 h / 25 °C
3.1: dmap / dichloromethane / 1 h / 25 °C
4.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C
4.2: 10 h / 25 °C
5.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C
5.2: pH 3
6.1: dichloromethane / 2 h / 25 °C
7.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 24 h / 25 °C
8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 110 °C
8.2: 20 °C
View Scheme
C55H54N4O7S3
1092363-38-6

C55H54N4O7S3

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diethylamine / dichloromethane / 3 h / 20 °C
2: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
3: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
4: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
C40H44N4O5S3
1191242-43-9

C40H44N4O5S3

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
2: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
3: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
(R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate
1092363-37-5

(R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
1.2: 0 - 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
3.1: diethylamine / dichloromethane / 3 h / 20 °C
4.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
5.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
(4R)-methyl 2-(2-((8S)-1-(9H-fluoren-9-yl)-5-isopropyl-3,6,10-trioxo-8-((E)-4-(tritylthio)-but-1-enyl)-2,7-dioxa-4,11-diazadodecan-12-yl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate
1092363-40-0

(4R)-methyl 2-(2-((8S)-1-(9H-fluoren-9-yl)-5-isopropyl-3,6,10-trioxo-8-((E)-4-(tritylthio)-but-1-enyl)-2,7-dioxa-4,11-diazadodecan-12-yl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
2: diethylamine / dichloromethane / 3 h / 20 °C
3: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
4: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
5: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
C10H13N3O2S2*ClH

C10H13N3O2S2*ClH

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dmap / dichloromethane / 0.08 h
1.2: 1 h
2.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
2.2: 0 - 20 °C
3.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
4.1: diethylamine / dichloromethane / 3 h / 20 °C
5.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
6.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
7.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
1.2: 0 - 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
3.1: diethylamine / dichloromethane / 3 h / 20 °C
4.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
5.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
2.1: diethylamine / acetonitrile / 2 h
2.2: 2 h
3.1: trifluoroacetic acid / dichloromethane / 20 °C
3.2: 16 h
4.1: dichloromethane / 2 h / 20 °C
5.1: trifluoroacetic acid; chlorotriisopropylsilane; triethylamine / dichloromethane
5.2: 2 h / 20 °C
View Scheme
(2E)-5-[(triphenylmethyl)thio]-2-pentenal
180973-22-2

(2E)-5-[(triphenylmethyl)thio]-2-pentenal

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C
1.2: 1 h / -78 °C
2.1: dmap / dichloromethane / 0.08 h
2.2: 1 h
3.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
3.2: 0 - 20 °C
4.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
5.1: diethylamine / dichloromethane / 3 h / 20 °C
6.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
7.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
8.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / -78 °C
2.1: 1H-imidazole / dichloromethane / 20 °C
2.2: 18 h
3.1: diethylamine / acetonitrile / 2 h
3.2: 2 h
4.1: trifluoroacetic acid / dichloromethane / 20 °C
4.2: 16 h
5.1: dichloromethane / 2 h / 20 °C
6.1: trifluoroacetic acid; chlorotriisopropylsilane; triethylamine / dichloromethane
6.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane
2.1: 1H-imidazole / dichloromethane / 20 °C
2.2: 18 h
3.1: diethylamine / acetonitrile / 2 h
3.2: 2 h
4.1: trifluoroacetic acid / dichloromethane / 20 °C
4.2: 16 h
5.1: dichloromethane / 2 h / 20 °C
6.1: trifluoroacetic acid; chlorotriisopropylsilane; triethylamine / dichloromethane
6.2: 2 h / 20 °C
View Scheme
(3S,4E)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanyl-hept-4-en-1-one
663918-95-4

(3S,4E)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-tritylsulfanyl-hept-4-en-1-one

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dmap / dichloromethane / 0.08 h
1.2: 1 h
2.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 °C
2.2: 0 - 20 °C
3.1: lithium hydroxide / tetrahydrofuran; water / 1.25 h / 0 °C
4.1: diethylamine / dichloromethane / 3 h / 20 °C
5.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 30 h / 20 °C
6.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
7.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
View Scheme
C2HF3O2*C10H13N3O2S2
1033814-01-5

C2HF3O2*C10H13N3O2S2

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dmap / dichloromethane / 1 h / 25 °C
2.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C
2.2: 10 h / 25 °C
3.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C
3.2: pH 3
4.1: dichloromethane / 2 h / 25 °C
5.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 24 h / 25 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 110 °C
6.2: 20 °C
View Scheme
C15H19N3O4S2
1033814-02-6

C15H19N3O4S2

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C
1.2: 10 h / 25 °C
2.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C
2.2: pH 3
3.1: dichloromethane / 2 h / 25 °C
4.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 24 h / 25 °C
5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 110 °C
5.2: 20 °C
View Scheme
C25H36N4O7S2
1033814-03-7

C25H36N4O7S2

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 0 °C
1.2: pH 3
2.1: dichloromethane / 2 h / 25 °C
3.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 24 h / 25 °C
4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 110 °C
4.2: 20 °C
View Scheme
C24H34N4O7S2
1033814-04-8

C24H34N4O7S2

largazole
1009815-87-5

largazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 2 h / 25 °C
2.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 24 h / 25 °C
3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 110 °C
3.2: 20 °C
View Scheme
largazole
1009815-87-5

largazole

Largazole thiol
1033814-08-2

Largazole thiol

Conditions
ConditionsYield
With ammonia In water; acetonitrile at 20℃; for 18h;70%
With ammonia In water; acetonitrile at 25℃; for 18h;70%
largazole
1009815-87-5

largazole

A

D-Val-OH
640-68-6

D-Val-OH

B

L-valine
72-18-4

L-valine

C

(S)-Malic acid
97-67-6

(S)-Malic acid

D

D(S)-2-methylcysteic acid
1127229-10-0

D(S)-2-methylcysteic acid

E

2-methylcysteic acid
1127229-09-7

2-methylcysteic acid

F

glycine
56-40-6

glycine

Conditions
ConditionsYield
Stage #1: largazole With ozone In dichloromethane at 25℃; for 0.5h;
Stage #2: With formic acid; dihydrogen peroxide at 70℃; for 0.333333h;
Stage #3: With hydrogenchloride; water at 110℃; for 24h;
...Expand

Largazole Specification

This chemical is called Largazole. With the molecular formula of C29H42N4O5S3, its molecular weight is 622.86. The CAS registry number of this chemical is 1009815-87-5. Additionally, this chemical should be stored at the temperature of -20°C. 

Other characteristics of the Largazole can be summarised as follows: (1)ACD/LogP: 7.06; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 7.062; (4)ACD/LogD (pH 7.4): 7.062; (5)ACD/BCF (pH 5.5): 137026.5; (6)ACD/BCF (pH 7.4): 137029.219; (7)ACD/KOC (pH 5.5): 165385.438; (8)ACD/KOC (pH 7.4): 165388.703; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 205.66 Å2; (13)Index of Refraction: 1.633; (14)Molar Refractivity: 168.795 cm3; (15)Molar Volume: 472.905 cm3; (16)Polarizability: 66.916×10-24 cm3; (17)Surface Tension: 51.017 dyne/cm; (18)Density: 1.317 g/cm3.

You can still convert the following datas into molecular structure:
1.SMILES: CCCCCCCC(=O)SCC/C=C/[C@@H]1CC(=O)NCc2nc(cs2)C3=N[C@@](CS3)(C(=O)N[C@H](C(=O)O1)C(C)C)C
2.InChI: InChI=1/C29H42N4O5S3/c1-5-6-7-8-9-13-24(35)39-14-11-10-12-20-15-22(34)30-16-23-31-21(17-40-23)26-33-29(4,18-41-26)28(37)32-25(19(2)3)27(36)38-20/h10,12,17,19-20,25H,5-9,11,13-16,18H2,1-4H3,(H,30,34)(H,32,37)/b12-10+/t20-,25+,29+/m1/s1
3.InChIKey: AXESYCSCGBQJBL-SZPBEECKBC

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