jaspamide Z₁

Base Information

• Chemical Name: jaspamide Z₁
• CAS No.: 161925-59-3
• Molecular Formula: C₃₆H₄₇BrN₄O₇
• Molecular Weight: 727.696
• Mol file: 161925-59-3.mol

Synonyms:jaspamide Z₁

Chemical Property of jaspamide Z₁

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of jaspamide Z₁

There total 57 articles about jaspamide Z₁ 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: 79.0%

jasplakinolide (119717-37-2,102396-24-7) → jaspamide Z1 (161925-59-3)

Guidance literature:

With potassium hydroxide; In methanol; at 40 - 50 ℃; for 5h;

DOI:10.1016/j.tet.2006.01.099

Reference yield: 78.0%

methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate (161925-58-2) → jaspamide Z1 (161925-59-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; for 144h; Ambient temperature;

DOI:10.1055/s-1995-3870

Reference yield:

(3S,4R,5S)-4-Iodo-3,5-dimethyl-dihydro-furan-2-one (134876-93-0) → jaspamide Z1 (161925-59-3)

Guidance literature:

Multi-step reaction with 11 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

11: ethanethiol, AlBr₃ / CH₂Cl₂ / 24 h / Ambient temperature

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

DOI:10.1021/jo00017a037

upstream raw materials:

(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

methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate

jasplakinolide

methyl 4-hydroxycinnamate

Downstream raw materials:

jasplakinolide