(E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

Base Information

• Chemical Name: (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester
• CAS No.: 134815-49-9
• Molecular Formula: C₄₄H₆₅BrN₄O₇Si
• Molecular Weight: 870.012
• Mol file: 134815-49-9.mol

Synonyms:(E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

Chemical Property of (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

There total 22 articles about (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester 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: 75.0%

(E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid (117289-84-6) + (R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester (134781-91-2) → (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester (134815-49-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 1.) -20 deg C to 0 deg C, 3 h, 2.) 4 deg C, 36 h;

DOI:10.1021/jo00017a037

Reference yield:

(3S,4R,5S)-4-Iodo-3,5-dimethyl-dihydro-furan-2-one (134876-93-0) → (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester (134815-49-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / H₂, Et₃N / 10percent Pd/C / diethyl ether; methanol / 0.5 h / 3309.7 Torr / Ambient temperature

2: DIBALH / diethyl ether; hexane / 0.5 h / -78 °C

3: pentane; diethyl ether / 1.) -78 deg C, 1 h, 2.) up to r.t., 3 h

4: 2.) 2.23 M KOH / 1.) xylenes, reflux, 8.5 h, 2.) ethylene glycol, 160-170 deg C, 12 h

5: 1.) imidazole, 2.) K₂CO₃ / 1.) DMF, 48 deg C, 12 h, 2.) EtOH, r.t., 1 h

6: 1.) KOH 2.) oxalyl chloride, pyridine / 1.) ether, 2 h 2.) benzene, 7 deg C, 1 h

7: n-BuLi / tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) r.t., 2 h

8: 1.)NaHMDS / 1.) THF, -78 deg C, 1 h, 2.) a) 1 h, -78 deg C, b) to r.t., 4 h , c) 2 h, r.t

9: 86 percent / 30percent H₂O₂, LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

10: 75 percent / DCC / CH₂Cl₂ / 1.) -20 deg C to 0 deg C, 3 h, 2.) 4 deg C, 36 h

With pyridine; 1H-imidazole; potassium hydroxide; lithium hydroxide; n-butyllithium; oxalyl dichloride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; pentane;

DOI:10.1021/jo00017a037

Reference yield:

para-iodoanisole (696-62-8) → (E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester (134815-49-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / NEt₃, Pd(OAc)2, tri-o-tolylphosphine / dimethylformamide / 24 h / Heating

2: 65 percent / NaBH₄, 9 N HCl / tetrahydrofuran; aq. ethanol / 1.) pH 7, -35 deg C, 1 h, 2.) -20 deg C, overnight

3: 81 percent / 4.5 N HCl / 2.5 h / 100 °C

4: 100 percent / HCl gas / 0 - 5 °C

5: 84 percent / triethylamine, DCC / tetrahydrofuran / Ambient temperature

6: 67 percent / trifluoroacetic acid / CH₂Cl₂ / 0.67 h / 0 °C

7: 75 percent / DCC / CH₂Cl₂ / 1.) -20 deg C to 0 deg C, 3 h, 2.) 4 deg C, 36 h

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; triethylamine; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00017a037

upstream raw materials:

(E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid

(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

(3S,4R,5S)-4-Iodo-3,5-dimethyl-dihydro-furan-2-one

para-iodoanisole

Downstream raw materials:

jasplakinolide

jaspamide Z₁

Refernces