jasplakinolide

Base Information

• Chemical Name: jasplakinolide
• CAS No.: 119717-37-2
• Molecular Formula: C₃₆H₄₅BrN₄O₆
• Molecular Weight: 709.68
• Mol file: 119717-37-2.mol

Synonyms:

Chemical Property of jasplakinolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of jasplakinolide

There total 100 articles about jasplakinolide 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: 93.0%

(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine ρ-lactone (161722-19-6) → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.3987/COM-94-S(B)52

Reference yield: 90.0%

C45H65N4O6SiBr (943858-43-3) → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1021/ol070855h

Reference yield:

C22H29NO5 → jasplakinolide (119717-37-2,102396-24-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 83 percent / LiBH₄ / ethanol; diethyl ether; tetrahydrofuran / 0.33 h / 0 °C

2.1: 24 mg / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 6 h / Heating

3.1: 81 percent / pyridine; AcOH; NaH₂PO₃*H₂O / Raney nickel / H₂O / 6 h / 50 °C

4.1: tetrahydrofuran / 0.5 h / 0 °C

5.1: triphenylphosphine; diisopropyl azodicarboxylate / diethyl ether / 10 h / 20 °C

6.1: 7.8 mg / potassium carbonate / ethanol / 5 h / 20 °C

7.1: 98 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

8.1: 95 percent / aq. lithium hydroxide / tetrahydrofuran; methanol / 6 h / 20 °C

9.1: 80 percent / DCC; HOBt / 24 h / 0 - 20 °C

10.1: 96 percent / aq. lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C

11.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

12.1: 80 percent / aq. potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 20 °C

13.1: DIPEA; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2.5 h / 20 °C

13.2: 82 percent / DMAP / benzene / 8 h

14.1: 90 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; 2,6-dimethylpyridine; lithium hydroxide; lithium borohydride; sodium dihydrogen phosphate; di-isopropyl azodicarboxylate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 2.1: Mitsunobu reaction / 5.1: Mitsunobu reaction;

DOI:10.1021/ol070855h

upstream raw materials:

jaspamide Z₁

(R)-3-((R)-3-(2-Bromo-1H-indol-3-yl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-methoxymethoxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine ρ-lactone

C₄₅H₆₅N₄O₆SiBr

Downstream raw materials:

jaspamide Z₁

(E)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid [1-({2-(2-bromo-1H-indol-3-yl)-1-[3-hydroxy-1-(4-hydroxy-phenyl)-propylcarbamoyl]-ethyl}-methyl-carbamoyl)-ethyl]-amide

Acetic acid 4-[(E)-7-(2-bromo-1H-indol-3-ylmethyl)-8,10,13,15,17,19-hexamethyl-2,6,9,12-tetraoxo-1-oxa-5,8,11-triaza-cyclononadec-15-en-4-yl]-phenyl ester