(7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone

Base Information

• Chemical Name: (7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone
• CAS No.: 53904-81-7
• Molecular Formula: C35H45NO11
• Molecular Weight: 655.742
• NSC Number: 146736
• Mol file: 53904-81-7.mol

Synonyms:(7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone;53904-81-7;NSC146736;NSC-146736

Chemical Property of (7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 968.5°C at 760 mmHg
• PKA: 4.77±0.70(Predicted)
• Flash Point: 539.5°C
• PSA: 221.92000
• Density: 1.38g/cm³
• LogP: 2.35570
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 1
• Exact Mass: 655.29926125
• Heavy Atom Count: 47
• Complexity: 1330

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=C(C(=O)NC2=CC(=O)C3=C(C(=C(C(=C3C2=O)O)C)O)C(=O)C(=CC(C(C(C(C(C(C(C1O)C)O)C)O)C)O)CO)C)C
• Isomeric SMILES: CC1/C=C/C=C(\C(=O)NC2=CC(=O)C3=C(C(=C(C(=C3C2=O)O)C)O)C(=O)/C(=C\C(C(C(C(C(C(C(C1O)C)O)C)O)C)O)CO)/C)/C

Technology Process of (7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone

There total 17 articles about (7Z,18E,20Z)-2,4,10,12,14,16-Hexahydroxy-9-(hydroxymethyl)-3,7,11,13,15,17,21-heptamethyl-23-azatricyclo[22.3.1.05,27]octacosa-1,3,5(27),7,18,20,24-heptaene-6,22,26,28-tetrone 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:

(E)-(2R,3R,4S,5S,6R,7R,8R,9S,10S)-2-(Bis-ethylsulfanyl-methyl)-4,6,8,10-tetramethyl-tridec-11-ene-1,3,5,7,9,13-hexaol (130432-90-5) → Rifamycin W (53904-81-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / pyridine / 4 h / 0 °C

2: conc. H₂SO₄ / acetone / 3 h / 25 °C

3: 96 percent / HgO, HgCl₂ / acetone; H₂O / 0.83 h / 25 °C

4: 1a) LiN(SiMe₃)2, 1b) ZnCl₂ / 1a) THF, -30 degC, 0.5 h, 1b) ether, -30 degC, 5 min, 2.) ether. o degC, 0.5 h

5: 85 percent / methanolic KOH / 44 h / 40 °C

6: 100 percent / MnO₂ / CH₂Cl₂ / 3 h / 25 °C

7: 95 percent / imidazol / CH₂Cl₂ / 1 h / 25 °C

8: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) THF, -78 degC, 10 min, 2.) -78 degC, 0.5 h

9: 98 percent / LiOH / tetrahydrofuran; H₂O; methanol / 8 h / 40 °C

10: 100 percent / Na₂S₂O₄, NaHCO₃ / dimethylformamide; H₂O / 0.17 h / 110 °C

11: 100 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr₂NEt / toluene / 3 h / 85 °C

12: 1.) AgO, 1N aq. HNO₃, 2.) 1N aq. HCl / 1.) dioxane, 25 degC, 1 h, 2.) THF, 25 degC, 2 d

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; silver(II) oxide; potassium hydroxide; lithium hydroxide; sodium dithionite; 18-crown-6 ether; sulfuric acid; nitric acid; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hexamethylsilazane; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4020(01)85586-1

Reference yield:

1-<5,8-dimethoxy-2,4-bis(methoxymethoxy)-3-methyl-6-nitro-1-naphthyl>-1-propanone (98291-49-7) → Rifamycin W (53904-81-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1a) LiN(SiMe₃)2, 1b) ZnCl₂ / 1a) THF, -30 degC, 0.5 h, 1b) ether, -30 degC, 5 min, 2.) ether. o degC, 0.5 h

2: 85 percent / methanolic KOH / 44 h / 40 °C

3: 100 percent / MnO₂ / CH₂Cl₂ / 3 h / 25 °C

4: 95 percent / imidazol / CH₂Cl₂ / 1 h / 25 °C

5: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) THF, -78 degC, 10 min, 2.) -78 degC, 0.5 h

6: 98 percent / LiOH / tetrahydrofuran; H₂O; methanol / 8 h / 40 °C

7: 100 percent / Na₂S₂O₄, NaHCO₃ / dimethylformamide; H₂O / 0.17 h / 110 °C

8: 100 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr₂NEt / toluene / 3 h / 85 °C

9: 1.) AgO, 1N aq. HNO₃, 2.) 1N aq. HCl / 1.) dioxane, 25 degC, 1 h, 2.) THF, 25 degC, 2 d

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; silver(II) oxide; potassium hydroxide; lithium hydroxide; sodium dithionite; 18-crown-6 ether; nitric acid; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hexamethylsilazane; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)85586-1

Reference yield:

2,2-Dimethyl-propionic acid (E)-(2R,3R,4S,5S,6R,7R,8R,9S,10S)-2-(bis-ethylsulfanyl-methyl)-13-(2,2-dimethyl-propionyloxy)-3,5,7,9-tetrahydroxy-4,6,8,10-tetramethyl-tridec-11-enyl ester (131755-72-1) → Rifamycin W (53904-81-7)

Guidance literature:

Multi-step reaction with 11 steps

1: conc. H₂SO₄ / acetone / 3 h / 25 °C

2: 96 percent / HgO, HgCl₂ / acetone; H₂O / 0.83 h / 25 °C

3: 1a) LiN(SiMe₃)2, 1b) ZnCl₂ / 1a) THF, -30 degC, 0.5 h, 1b) ether, -30 degC, 5 min, 2.) ether. o degC, 0.5 h

4: 85 percent / methanolic KOH / 44 h / 40 °C

5: 100 percent / MnO₂ / CH₂Cl₂ / 3 h / 25 °C

6: 95 percent / imidazol / CH₂Cl₂ / 1 h / 25 °C

7: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) THF, -78 degC, 10 min, 2.) -78 degC, 0.5 h

8: 98 percent / LiOH / tetrahydrofuran; H₂O; methanol / 8 h / 40 °C

9: 100 percent / Na₂S₂O₄, NaHCO₃ / dimethylformamide; H₂O / 0.17 h / 110 °C

10: 100 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, i-Pr₂NEt / toluene / 3 h / 85 °C

11: 1.) AgO, 1N aq. HNO₃, 2.) 1N aq. HCl / 1.) dioxane, 25 degC, 1 h, 2.) THF, 25 degC, 2 d

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; silver(II) oxide; potassium hydroxide; lithium hydroxide; sodium dithionite; 18-crown-6 ether; sulfuric acid; nitric acid; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hexamethylsilazane; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4020(01)85586-1

upstream raw materials:

C₅₃H₈₁NO₁₃Si

(E)-(2R,3R,4S,5S,6R,7R,8R,9S,10S)-2-(Bis-ethylsulfanyl-methyl)-4,6,8,10-tetramethyl-tridec-11-ene-1,3,5,7,9,13-hexaol

1-<5,8-dimethoxy-2,4-bis(methoxymethoxy)-3-methyl-6-nitro-1-naphthyl>-1-propanone

2,2-Dimethyl-propionic acid (E)-(2R,3R,4S,5S,6R,7R,8R,9S,10S)-2-(bis-ethylsulfanyl-methyl)-13-(2,2-dimethyl-propionyloxy)-3,5,7,9-tetrahydroxy-4,6,8,10-tetramethyl-tridec-11-enyl ester

Refernces

• 1、 Nakata,Akiyama,Kamata -i.,Kojima,Masuda Kinoshita,Tatsuta. "The total synthesis of rifamycin W". . p. 4629 - 4652. Retrieved 2007/10/02.