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1009815-87-5

Basic Information
CAS No.: 1009815-87-5
Name: Largazole
Article Data: 18
Cas Database
Molecular Structure:
Molecular Structure of 1009815-87-5 (Largazole)
Formula: C29H42N4O5S3
Molecular Weight: 622.874
Synonyms: Largazole
Density: 1.317 g/cm3
PSA: 212.64000
LogP: 5.02170
Synthetic route
1033814-08-2

Largazole thiol

111-64-8

n-octanoic acid chloride

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%
1263375-82-1

C58H64N4O8S3

A

1009815-87-5

largazole

B

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
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

1009815-87-5

largazole

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

S-but-3-enyl octanethionate

1033813-96-5

C19H24N4O4S2

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%
1033813-95-4

S-but-3-enyl octanethionate

1033813-96-5

C19H24N4O4S2

A

1009815-87-5

largazole

B

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;

C29H44N4O6S3

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

A

1009815-87-5

largazole

B

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

A

1009815-87-5

largazole

B

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
297165-32-3

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

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
1033814-13-9

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

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
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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