Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel-

Base Information

• Chemical Name: Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel-
• CAS No.: 127180-77-2
• Molecular Formula: C₂₉H₃₀N₄O₈
• Molecular Weight: 562.579
• DSSTox Substance ID: DTXSID701098368
• Mol file: 127180-77-2.mol

Synonyms:DTXSID701098368;127180-77-2;Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel-

Chemical Property of Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel-

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 562.20636393
• Heavy Atom Count: 41
• Complexity: 1540

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=C(C1=O)CC3C4C5=C(CC(N4C)C(N3C2CNC(=O)C(=O)C)C#N)C(=O)C(=C(C5=O)OC)C)OC
• Isomeric SMILES: CC1=C(C(=O)C2=C(C1=O)C[C@@H]3[C@@H]4C5=C(C[C@@H](N4C)[C@H](N3[C@@H]2CNC(=O)C(=O)C)C#N)C(=O)C(=C(C5=O)OC)C)OC

Technology Process of Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel-

There total 27 articles about Propanamide, N-[[(6R,7S,9S,14aR,15S)-7-cyano-1,5,6,7,9,10,13,14,14a,15-decahydro-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-6,15-imino-4H-isoquino[3,2-b][3]benzazocin-9-yl]methyl]-2-oxo-, rel- 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: 60.0%

C31H38N4O8 (127103-59-7) → (+/-)-Saframycin A (66082-27-7,127180-77-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetone; at 0 ℃;

DOI:10.1021/ja00165a095

Reference yield: 20.0%

N-(((6S*,7R*,9R*,14aS*,15R*)-7-cyano-1,2,4,10,11,13-hexamethoxy-3,12,16-trimethyl-6,7,9,14,14a,15-hexahydro-5H-6,15-iminobenzo[4,5]azocino[1,2-b]isoquinolin-9-yl)methyl)-2-oxopropanamide → (+/-)-Saframycin A (66082-27-7,127180-77-2)

Guidance literature:

N-(((6S*,7R*,9R*,14aS*,15R*)-7-cyano-1,2,4,10,11,13-hexamethoxy-3,12,16-trimethyl-6,7,9,14,14a,15-hexahydro-5H-6,15-iminobenzo[4,5]azocino[1,2-b]isoquinolin-9-yl)methyl)-2-oxopropanamide; With boron tribromide; In dichloromethane; at -78 - -20 ℃; for 21h;

With ammonium cerium (IV) nitrate; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2018.07.017

Reference yield:

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde (82622-02-4) → (+/-)-Saframycin A (66082-27-7,127180-77-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 86 percent / t-BuOK, t-BuOH / tetrahydrofuran / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 80 °C / 51714.8 Torr

3: Et₃N / CH₂Cl₂ / Heating

4: Et₃N, DMAP / CH₂Cl₂ / -15 °C

5: 1.) t-BuOK, t-BuOH, 2.) DBU / 1.) THF, -78 deg C, 2.) 0 deg C

7: 99 percent / H₂ / Raney Ni-W₂ / ethanol / 120 °C / 77572.2 Torr

8: 85 percent / NaBH₃CN, TFA / methanol / 23 °C

9: 1.) DMAP, 2.) NaBH₄ / 1.) DMF, 60 deg C, 2.) EtOH, 0 deg C

10: TFA / 23 °C

11: methanol / 60 °C

12: 1.) (COCl)2, DMSO, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) MeOH, 23 deg C

13: TFA / 23 °C

14: NaHCO₃ / CH₂Cl₂ / 23 °C

15: 60 percent / DDQ / acetone; H₂O / 0 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; palladium on activated charcoal; Raney Ni-W₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1021/ja00165a095

upstream raw materials:

C₃₁H₃₈N₄O₈

5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde

1-Acetyl-3-(5-hydroxy-2,4-dimethoxy-3-methyl-benzyl)-piperazine-2,5-dione

1-Acetyl-3-[1-(5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione

Downstream raw materials:

(+)-saframycin F

(-)-saframycin G

(+)-5-epi-saframycin G