Biphenomycin B

Base Information

• Chemical Name: Biphenomycin B
• CAS No.: 100217-74-1
• Molecular Formula: C₂₃H₂₈N₄O₇
• Molecular Weight: 472.498
• DSSTox Substance ID: DTXSID80143025
• Nikkaji Number: J91.885G
• Wikidata: Q83006675
• Mol file: 100217-74-1.mol

Synonyms:biphenomycin B

Chemical Property of Biphenomycin B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 953.3°Cat760mmHg
• Flash Point: 530.3°C
• PSA: 215.21000
• Density: 1.359g/cm³
• LogP: 0.90700
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 472.19579924
• Heavy Atom Count: 34
• Complexity: 738

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)NC(C(=O)NC(CC2=C(C=CC(=C2)C3=CC1=C(C=C3)O)O)C(=O)O)CC(CN)O)N
• Isomeric SMILES: C1[C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC2=C(C=CC(=C2)C3=CC1=C(C=C3)O)O)C(=O)O)C[C@H](CN)O)N

Technology Process of Biphenomycin B

There total 25 articles about Biphenomycin B 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: 70.0%

benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate (134038-87-2) → biphenomycin B (100217-74-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1039/c39910000275

Reference yield: 52.0%

C33H38N4O9 (1313436-87-1) → biphenomycin B (100217-74-1)

Guidance literature:

With boron tribromide; In dichloromethane; for 24h; Inert atmosphere;

DOI:10.1039/b811583d

Reference yield:

2-benzyloxy-5-bromobenzaldehyde (121124-94-5) → biphenomycin B (100217-74-1)

Guidance literature:

Multi-step reaction with 19 steps

1: 81 percent / BF₃*Et₂O / toluene / 4 h / Heating

3: 74 percent / N-bromosuccinimide (NBS), 2,6-lutidine, H₂O / acetonitrile / 0.08 h / 0 °C

4: 99 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 1 h / Ambient temperature

5: 95 percent / NEt₃/C / ethanol; CHCl₃ / 48 h / Ambient temperature

6: 100 percent / LiOH, H₂O / dioxane / 12 h / Ambient temperature

7: 100 percent / H₂, <(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>⁺*BF₄^- / methanol / 72 h / Ambient temperature

8: 82 percent / dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) / ethyl acetate / 12 h / -15 - 20 °C

9: 84 percent / pyridinium-p-toluene sulphonate, H₂O / acetone / 6 h / Heating

10: 93 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 2 h / Ambient temperature

11: NEt₃/C / ethanol; CHCl₃ / 48 h / Ambient temperature

12: H₂, <(R,R)-1,2-bis<2-(2-methoxyphenyl)phenylphosphino>ethane>>⁺*BF₄^- / methanol / 72 h / Ambient temperature

13: 100 percent / 6 M HCl / dioxane / 2 h / 20 °C

14: 71 percent / N-(3-dimethylaminopropyl)-N'-ethylcarboimide hydrochloride (EDC), hydroxybenzotriazole / CH₂Cl₂ / 14 h / 15 - 20 °C

15: 85 percent / AcOH, H₂O / 7 h / 50 °C

16: Bu₄NF / dimethylformamide / 1 h / Ambient temperature

17: 95 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 14 h / -15 - 20 °C

18: 1.) 6 M HCl, 2.) NaHCO₃ / 1.) dioxane, CH₂Cl₂, 0 deg C, 2.) CHCl₃, 20 deg C, 5 min

19: 70 percent / trimethylsilyl trifluoromethane sulphonate, thioanisole, CF₃CO₂H / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; N-Bromosuccinimide; [Rh((R,R)-DIPAMP)(COD)]BF₄; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; NEt₃/C; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium chloride; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1039/c39910000275

upstream raw materials:

benzyl 5,17-bisbenzyloxy-14(S)-benzyloxycarbonylamino-11(S)-(3-benzyloxycarbonylamino-2(R)-hydroxypropyl)-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]-henicosa-1(19),2,4,6(21),16(20),17-hexaene-8(S)-carboxylate

2-benzyloxy-5-bromobenzaldehyde

benzyl 2(S)-(5-benzyloxycarbonylamino-2(S)-tert-butoxycarbonylamino-4(R)-hydroxypentanoylamino)-3-[4,4'-bisbenzyloxy-3'-(2(S)-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonylethyl)biphenyl-3-yl]propionate

2-benzyloxy-5-iodobenzaldehyde

Refernces

• 1、 Schmidt, Ulrich,Meyer, Regina,Leitenberger, Volker,Lieberknecht, Albrecht,Griesser, Helmut. "The Synthesis of Biphenomycin B". . p. 275 - 277. Retrieved 2007/10/02.