(1R,2Z,4E,6E,10S,12E,16S,21S)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione

Base Information

• Chemical Name: (1R,2Z,4E,6E,10S,12E,16S,21S)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione
• CAS No.: 77642-19-4
• Molecular Formula: C29H35 N O5
• Molecular Weight: 477.601
• UNII: LDW8TT2M3F
• DSSTox Substance ID: DTXSID60894881
• Wikipedia: Hitachimycin
• Metabolomics Workbench ID: 144269
• Mol file: 77642-19-4.mol

Synonyms:hitachimycin;stubomycin

Chemical Property of (1R,2Z,4E,6E,10S,12E,16S,21S)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione

Chemical Property:

• Vapor Pressure: 8.11E-22mmHg at 25°C
• Boiling Point: 721°C at 760 mmHg
• Flash Point: 389.8°C
• PSA: 95.86000
• Density: 1.2g/cm³
• LogP: 5.13860
• XLogP3: 4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 477.25152322
• Heavy Atom Count: 35
• Complexity: 891

Purity/Quality:

95% ^*data from raw suppliers

HITACHIMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2CC(C(=C2C(=O)CC(CCC=CCC(NC(=O)C=CC=C1)C3=CC=CC=C3)O)O)OC
• Isomeric SMILES: C/C/1=C/[C@H]2C[C@@H](C(=C2C(=O)C[C@H](CC/C=C/C[C@H](NC(=O)/C=C\C=C1)C3=CC=CC=C3)O)O)OC

Technology Process of (1R,2Z,4E,6E,10S,12E,16S,21S)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione

There total 37 articles about (1R,2Z,4E,6E,10S,12E,16S,21S)-16,20-dihydroxy-21-methoxy-3-methyl-10-phenyl-9-azabicyclo[17.3.0]docosa-2,4,6,12,19-pentaene-8,18-dione 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: 64.0%

(4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,18-Dihydroxy-2-methoxy-11-(4-methoxy-benzyl)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione (124944-58-7) → (+)-hitachimycin (77642-19-4)

Guidance literature:

With trifluoroacetic acid; for 2.5h; Ambient temperature;

DOI:10.1021/jo00291a005

Reference yield:

{(S)-3-[(4-Methoxy-benzyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propyl}-triphenyl-phosphonium; iodide (124944-47-4) → (+)-hitachimycin (77642-19-4)

Guidance literature:

Multi-step reaction with 20 steps

1: n-butyllithium, LiBr / tetrahydrofuran / 0.75 h / 0 °C

2: 2.) phenyllithium, 3.) t-BuOK

3: 96 percent / CH₃COOH, H₂O / tetrahydrofuran / 1 h / Ambient temperature

4: 80 percent / pyridine / 48 h / Ambient temperature

5: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h

6: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min

7: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min

8: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C

9: 99 percent / K₂CO₃ / tetrahydrofuran; toluene

10: 85 percent / MeI, H₂O / acetonitrile / Ambient temperature

11: 1.) t-BuLi, 2.) dineopentylzinc

12: (CH₃)2SO, pyridine, CF₃COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature

13: benzene; diethyl ether / 0.33 h

14: n-Bu₄NF / tetrahydrofuran / 0.25 h / 0 °C

15: 75percent aq. CH₃COOH / tetrahydrofuran / 0 - 5 °C

16: 68 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.5 h / 0 °C

17: 86 percent / (COCl)2, (CH₃)2SO / CH₂Cl₂ / 0.33 h / -78 °C

18: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C

19: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

20: 64 percent / CF₃COOH / 2.5 h / Ambient temperature

With pyridine; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; diethyl cyanophosphonate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; water; tert.-butyl lithium; potassium hydride; sodium naphthalenide; sodium hydride; dineopentylzinc; potassium carbonate; acetic acid; dimethyl sulfoxide; phenyllithium; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00047a008

Reference yield:

(4-Methoxy-benzyl)-[(E)-(1S,7S)-7-(4-methoxy-benzyloxy)-9-oxo-1-phenyl-non-3-enyl]-carbamic acid 2-trimethylsilanyl-ethyl ester (124944-50-9) → (+)-hitachimycin (77642-19-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) t-BuLi, 2.) dineopentylzinc

2: (CH₃)2SO, pyridine, CF₃COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature

3: benzene; diethyl ether / 0.33 h

4: n-Bu₄NF / tetrahydrofuran / 0.25 h / 0 °C

5: 75percent aq. CH₃COOH / tetrahydrofuran / 0 - 5 °C

6: 68 percent / diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.5 h / 0 °C

7: 86 percent / (COCl)2, (CH₃)2SO / CH₂Cl₂ / 0.33 h / -78 °C

8: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C

9: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 64 percent / CF₃COOH / 2.5 h / Ambient temperature

With pyridine; oxalyl dichloride; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; dineopentylzinc; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00047a008

upstream raw materials:

(4Z,6E,8E,14E)-(2S,3aR,12S,18S)-1,18-Dihydroxy-2-methoxy-11-(4-methoxy-benzyl)-5-methyl-12-phenyl-3,3a,12,13,16,17,18,19-octahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

maleic anhydride

(S)-(-)-5-methoxycyclopent-2-en-1-one

Downstream raw materials:

Acetic acid (4Z,6E,8E,14E)-18-acetoxy-2-methoxy-5-methyl-10,20-dioxo-12-phenyl-2,3,3a,10,11,12,13,16,17,18,19,20-dodecahydro-11-aza-cyclopentacyclononadecen-1-yl ester

Acetic acid (Z)-18,20-diacetoxy-2-methoxy-5-methyl-10-oxo-12-phenyl-1,2,3,3a,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,20a-icosahydro-11-aza-cyclopentacyclononadecen-1-yl ester

1,18-Dihydroxy-2-methoxy-5-methyl-12-phenyl-3,3a,4,5,6,7,8,9,12,13,14,15,16,17,18,19-hexadecahydro-2H,11H-11-aza-cyclopentacyclononadecene-10,20-dione

tetrahydrohitachimycin

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