Antibiotic DC 107

Base Information

• Chemical Name: Antibiotic DC 107
• CAS No.: 120500-15-4
• Molecular Formula: C22H26 N2 O6 S3
• Molecular Weight: 510.656
• Wikipedia: Leinamycin
• Mol file: 120500-15-4.mol

Synonyms:DC 107;DC-107;leinamycin

Chemical Property of Antibiotic DC 107

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 10.23±0.70(Predicted)
• Flash Point: °C
• PSA: 206.41000
• Density: 1.48g/cm³
• LogP: 3.57130
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 0
• Exact Mass: 510.09530007
• Heavy Atom Count: 33
• Complexity: 935

Purity/Quality:

99.90% ^*data from raw suppliers

LEINAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=NC(=CS2)C=CC=CC(=O)C(C=C(CCC3(CC(=O)N1)C(C(=O)SS3=O)(C)O)C)O
• Isomeric SMILES: CC1C2=NC(=CS2)/C=C\C=C/C(=O)C(/C=C(\CCC3(CC(=O)N1)C(C(=O)SS3=O)(C)O)/C)O

Technology Process of Antibiotic DC 107

There total 41 articles about Antibiotic DC 107 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

C22H26N2O5S3 (127183-14-6) → leinamycin (120500-15-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 ℃; for 0.75h;

DOI:10.1021/ja00071a066

Reference yield:

Ethyl (S)-2-(1-hydroxyethyl)-thiazole-4-carboxylate (111946-69-1) → leinamycin (120500-15-4)

Guidance literature:

Multi-step reaction with 27 steps

1: imidazole / dimethylformamide / 24 h / 23 °C

2: LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

3: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

4: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

5: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

6: n-Bu₄NF / tetrahydrofuran / 2 h / 0 °C

7: 99 percent / N₃H, PPh₃, DEAD / toluene / 0.33 h / 0 °C

8: 88 percent / PdCl₂(PPh₃)2, CuBr, Et₃N / tetrahydrofuran / 0.5 h / 23 °C

9: 99 percent / Zn, AcOH / ethanol / 0.5 h / 23 °C

10: 74 percent / H₂, quinoline / Lindlar catalyst / methanol / 2 h / 23 °C

11: 99 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 1.5 h / 23 °C

12: 91 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr₂NEt / toluene / 0.33 h / 60 °C

13: 1.) n-BuLi, 2.) Al(Hg), H₂O / 1.) from -78 deg C to 0 deg C, 30 min, 2.) THF, 23 deg C, 40 min

14: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 11 h / Heating

15: N-bromosuccinimide / acetonitrile; H₂O / 0.08 h / 0 °C

16: 10percent aq. HClO₄ / tetrahydrofuran / 8 h / 23 °C

17: 80 percent / H₂S, Et₃N / tetrahydrofuran / 2 h / 23 °C

18: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.75 h / 23 °C

19: 94 percent / i-Am-ONO, NaOMe / 1.5 h / 23 °C

20: 94 percent / pyridine / methanol / 0.5 h / 23 °C

21: pyridine / CH₂Cl₂ / 0.17 h / 23 °C

22: KH / tetrahydrofuran / 0.5 h / 23 °C

23: NaSH / tetrahydrofuran / 0.33 h / 23 °C

24: I₂ / tetrahydrofuran / 23 °C

25: 64 percent / 35percent aq. HCHO, 3N aq. HCl / acetone / 77 h / 23 °C

26: 61 percent / 2N aq. HCl, AcOH / 0.75 h / 0 °C

27: 84 percent / m-chloroperoxybenzoic acid ( / tetrahydrofuran / 0.75 h / 0 °C

With pyridine; 1H-imidazole; quinoline; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; aluminum amalgam; N-Bromosuccinimide; sodium hydrogensulfide; lithium aluminium tetrahydride; n-butyllithium; formaldehyd; hydrogen azide; perchloric acid; oxalyl dichloride; hydrogen sulfide; tetrabutyl ammonium fluoride; water; hydrogen; iodine; sodium methylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; zinc; diethylazodicarboxylate; isopentyl nitrite; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ja00071a066

Reference yield:

(S)-1-(4-Ethynyl-thiazol-2-yl)-ethanol → leinamycin (120500-15-4)

Guidance literature:

Multi-step reaction with 21 steps

1: 99 percent / N₃H, PPh₃, DEAD / toluene / 0.33 h / 0 °C

2: 88 percent / PdCl₂(PPh₃)2, CuBr, Et₃N / tetrahydrofuran / 0.5 h / 23 °C

3: 99 percent / Zn, AcOH / ethanol / 0.5 h / 23 °C

4: 74 percent / H₂, quinoline / Lindlar catalyst / methanol / 2 h / 23 °C

5: 99 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 1.5 h / 23 °C

6: 91 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr₂NEt / toluene / 0.33 h / 60 °C

7: 1.) n-BuLi, 2.) Al(Hg), H₂O / 1.) from -78 deg C to 0 deg C, 30 min, 2.) THF, 23 deg C, 40 min

8: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 11 h / Heating

9: N-bromosuccinimide / acetonitrile; H₂O / 0.08 h / 0 °C

10: 10percent aq. HClO₄ / tetrahydrofuran / 8 h / 23 °C

11: 80 percent / H₂S, Et₃N / tetrahydrofuran / 2 h / 23 °C

12: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 0.75 h / 23 °C

13: 94 percent / i-Am-ONO, NaOMe / 1.5 h / 23 °C

14: 94 percent / pyridine / methanol / 0.5 h / 23 °C

15: pyridine / CH₂Cl₂ / 0.17 h / 23 °C

16: KH / tetrahydrofuran / 0.5 h / 23 °C

17: NaSH / tetrahydrofuran / 0.33 h / 23 °C

18: I₂ / tetrahydrofuran / 23 °C

19: 64 percent / 35percent aq. HCHO, 3N aq. HCl / acetone / 77 h / 23 °C

20: 61 percent / 2N aq. HCl, AcOH / 0.75 h / 0 °C

21: 84 percent / m-chloroperoxybenzoic acid ( / tetrahydrofuran / 0.75 h / 0 °C

With pyridine; quinoline; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; aluminum amalgam; N-Bromosuccinimide; sodium hydrogensulfide; n-butyllithium; formaldehyd; hydrogen azide; perchloric acid; hydrogen sulfide; water; hydrogen; iodine; sodium methylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; zinc; diethylazodicarboxylate; isopentyl nitrite; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1021/ja00071a066

upstream raw materials:

C₂₂H₂₆N₂O₅S₃

Ethyl (S)-2-(1-hydroxyethyl)-thiazole-4-carboxylate

2-((R)-1-Azido-ethyl)-4-ethynyl-thiazole

2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(2,2-dibromo-vinyl)-thiazole

Refernces