Bouvardin, 5-(N-methyl-L-tyrosine)-

Base Information

• Chemical Name: Bouvardin, 5-(N-methyl-L-tyrosine)-
• CAS No.: 64725-24-2
• Molecular Formula: C40H48 N6 O9
• Molecular Weight: 756.856
• Mol file: 64725-24-2.mol

Synonyms:deoxybouvardin;RA V;RA-V

Chemical Property of Bouvardin, 5-(N-methyl-L-tyrosine)-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1083.3°Cat760mmHg
• PKA: 9.11±0.70(Predicted)
• Flash Point: 609°C
• PSA: 186.92000
• Density: 1.189g/cm³
• LogP: 2.34320
• Hydrogen Bond Donor Count: 21
• Hydrogen Bond Acceptor Count: 41
• Rotatable Bond Count: 12
• Exact Mass: 3116.4492868
• Heavy Atom Count: 225
• Complexity: 1400

Purity/Quality:

99%min ^*data from raw suppliers

RA-V ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N(C2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC(C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.CC1C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N(C2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC(C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.CC1C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N(C2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC(C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.CC1C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N(C2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC(C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.O.O.O.O.O
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@@H](C(=O)N([C@@H]2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)C[C@H](C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.C[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@@H](C(=O)N([C@@H]2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)C[C@H](C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.C[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@@H](C(=O)N([C@@H]2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)C[C@H](C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.C[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@@H](C(=O)N([C@@H]2CC3=CC=C(C=C3)OC4=C(C=CC(=C4)C[C@H](C(=O)N1)N(C2=O)C)O)C)C)CC5=CC=C(C=C5)OC)C)C.O.O.O.O.O

Technology Process of Bouvardin, 5-(N-methyl-L-tyrosine)-

There total 38 articles about Bouvardin, 5-(N-methyl-L-tyrosine)- 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%

RA-VII (122621-60-7,144993-87-3,144993-88-4,86229-97-2) → deoxybouvadin (64725-24-2)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.43.1325

Reference yield:

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) → deoxybouvadin (64725-24-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / NaH / dimethylformamide / 6 h / 0 - 25 °C

2: EDCI, HOBt*H₂O / dimethylformamide / 16 h / 25 °C

3: 1.) NaH, CuBr, SMe₂ / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h

4: 97 percent / 3.0 M aq. HCl / ethyl acetate / 1 h / 25 °C

5: 53 percent / EDCI, HOBt*H₂O / dimethylformamide / 12 h / 25 °C

6: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C

7: 3 N HCl / ethyl acetate / 1 h / 25 °C

8: 58 percent / NaHCO₃, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C

9: 57 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 - 20 °C

With hydrogenchloride; lithium hydroxide; dimethylsulfide; diphenyl phosphoryl azide; boron tribromide; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(I) bromide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00062a004

Reference yield:

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → deoxybouvadin (64725-24-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 6 h / Heating

2: m-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 24 h / 40 °C

3: HCl / methanol / 3 h / 25 °C

4: H₂ / 10percent Pd/C / methanol / 6 h / 25 °C

5: EDCI, HOBt*H₂O / dimethylformamide / 16 h / 25 °C

6: 1.) NaH, CuBr-SMe₂ / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h

7: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C

8: 53 percent / EDCI, HOBt*H₂O / dimethylformamide / 12 h / 25 °C

9: aq. LiOH / tetrahydrofuran; methanol / 2 h / 25 °C

10: 3 N HCl / ethyl acetate / 1 h / 25 °C

11: 58 percent / NaHCO₃, diphenyl phosphoroazidate (DPPA) / dimethylformamide / 72 h / 0 °C

12: 57 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 - 20 °C

With hydrogenchloride; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; boron tribromide; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00062a004

upstream raw materials:

RA-VII

diazomethyl-trimethyl-silane

N-methyl-L-tyrosine

L,L-N,N-dimethylcycloisodityrosine methyl ester

Downstream raw materials:

C₄₇H₅₁ClN₆O₁₀

C₄₂H₅₀N₆O₁₀

C₄₄H₅₄N₆O₁₀

C₅₈H₈₂N₆O₁₀

Refernces

• 1、 Inoue,Inaba,Umezawa,Yuasa,Itokawa,Ogura,Komatsu,Hara,Hoshino. "Regioselective synthesis of 14-membered biaryl ethers: Total synthesis of RA-VII and deoxybouvardin". . p. 1325 - 1335. Retrieved 2007/10/02.
• 2、 Boger,Yohannes. "Total synthesis of deoxybouvardin and RA-VII: Macrocyclization via an intramolecular Ullmann reaction". . p. 1427 - 1429. Retrieved 2007/10/02.