(6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

Base Information

• Chemical Name: (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester
• CAS No.: 272121-01-4
• Molecular Formula: C₄₁H₆₁N₃O₈Se
• Molecular Weight: 802.911
• Mol file: 272121-01-4.mol

Synonyms:

Chemical Property of (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester

There total 24 articles about (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl 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:

4,4-dimethyl-2-pentyne (999-78-0) → (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (272121-01-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: tetrahydrofuran / 1.5 h / Heating

2.1: H₂O

3.1: 1.178 g / Cs₂CO₃; AsPh₃ / PdCl₂(dppf)2*CH₂Cl₂ / tetrahydrofuran / 24 h / 20 °C

4.1: chemical manganese dioxide / CH₂Cl₂ / 4 h / 20 °C

5.1: dibutylboryl triflate; Et₃N / CH₂Cl₂ / 0 - 3 °C

5.2: 5.609 g / CH₂Cl₂ / 1 h / -78 - -5 °C

6.1: 88 percent / CH₂Cl₂; methanol / 0.17 h / -30 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 2.75 h / 0 - 20 °C

8.1: 1.04 g / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 - 0 °C

9.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; MS₄A / acetonitrile / 0.42 h / 0 - 20 °C

10.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / -78 °C

10.2: 907 mg / tetrahydrofuran; toluene / 0.67 h / -78 - -10 °C

11.1: 76 percent / TFA / CH₂Cl₂ / 22.5 h / -10 - 20 °C

12.1: 68 percent / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.1: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

14.1: KHCO₃ / dimethylformamide / 3 h / 20 °C

15.1: 86 mg / EDCI*HCl; DMAP / CH₂Cl₂ / 13 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; lithium hydroxide; tetrapropylammonium perruthennate; 18-crown-6 ether; triphenyl-arsane; di-n-butylboryl trifluoromethanesulfonate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; caesium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Addition / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Oxidation / 5.1: enolisation, boration / 5.2: Addition / 6.1: Substitution / 7.1: Substitution / 8.1: Reduction / 9.1: Oxidation / 10.1: deprotonation, Still-Horner olefination / 10.2: Condensation / 11.1: ether cleavage, lactonization / 12.1: Addition / 13.1: Hydrolysis / 14.1: Esterification / 15.1: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

Reference yield:

2-((Z)-1,3,3-trimethyl-but-1-enyl)-benzo[1,3,2]dioxaborole (37490-30-5) → (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (272121-01-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: H₂O

2.1: 1.178 g / Cs₂CO₃; AsPh₃ / PdCl₂(dppf)2*CH₂Cl₂ / tetrahydrofuran / 24 h / 20 °C

3.1: chemical manganese dioxide / CH₂Cl₂ / 4 h / 20 °C

4.1: dibutylboryl triflate; Et₃N / CH₂Cl₂ / 0 - 3 °C

4.2: 5.609 g / CH₂Cl₂ / 1 h / -78 - -5 °C

5.1: 88 percent / CH₂Cl₂; methanol / 0.17 h / -30 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 2.75 h / 0 - 20 °C

7.1: 1.04 g / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 - 0 °C

8.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; MS₄A / acetonitrile / 0.42 h / 0 - 20 °C

9.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / -78 °C

9.2: 907 mg / tetrahydrofuran; toluene / 0.67 h / -78 - -10 °C

10.1: 76 percent / TFA / CH₂Cl₂ / 22.5 h / -10 - 20 °C

11.1: 68 percent / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

12.1: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

13.1: KHCO₃ / dimethylformamide / 3 h / 20 °C

14.1: 86 mg / EDCI*HCl; DMAP / CH₂Cl₂ / 13 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; lithium hydroxide; tetrapropylammonium perruthennate; 18-crown-6 ether; triphenyl-arsane; di-n-butylboryl trifluoromethanesulfonate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; caesium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Hydrolysis / 2.1: Substitution / 3.1: Oxidation / 4.1: enolisation, boration / 4.2: Addition / 5.1: Substitution / 6.1: Substitution / 7.1: Reduction / 8.1: Oxidation / 9.1: deprotonation, Still-Horner olefination / 9.2: Condensation / 10.1: ether cleavage, lactonization / 11.1: Addition / 12.1: Hydrolysis / 13.1: Esterification / 14.1: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

Reference yield:

C7H15BO2 → (6E,8E)-(3S,4R,5S)-5-(2-{(S)-2-[((S)-2-Allyloxycarbonylamino-propionyl)-methyl-amino]-3-methyl-butyrylamino}-acetoxy)-4,6,8,10,10-pentamethyl-3-phenylselanylmethyl-undeca-6,8-dienoic acid allyl ester (272121-01-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1.178 g / Cs₂CO₃; AsPh₃ / PdCl₂(dppf)2*CH₂Cl₂ / tetrahydrofuran / 24 h / 20 °C

2.1: chemical manganese dioxide / CH₂Cl₂ / 4 h / 20 °C

3.1: dibutylboryl triflate; Et₃N / CH₂Cl₂ / 0 - 3 °C

3.2: 5.609 g / CH₂Cl₂ / 1 h / -78 - -5 °C

4.1: 88 percent / CH₂Cl₂; methanol / 0.17 h / -30 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 2.75 h / 0 - 20 °C

6.1: 1.04 g / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 - 0 °C

7.1: N-methylmorpholine N-oxide; tetrapropylammonium perruthenate; MS₄A / acetonitrile / 0.42 h / 0 - 20 °C

8.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / -78 °C

8.2: 907 mg / tetrahydrofuran; toluene / 0.67 h / -78 - -10 °C

9.1: 76 percent / TFA / CH₂Cl₂ / 22.5 h / -10 - 20 °C

10.1: 68 percent / HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.1: LiOH; H₂O / tetrahydrofuran / 1.5 h / 0 °C

12.1: KHCO₃ / dimethylformamide / 3 h / 20 °C

13.1: 86 mg / EDCI*HCl; DMAP / CH₂Cl₂ / 13 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; manganese(IV) oxide; lithium hydroxide; tetrapropylammonium perruthennate; 18-crown-6 ether; triphenyl-arsane; di-n-butylboryl trifluoromethanesulfonate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; caesium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Substitution / 2.1: Oxidation / 3.1: enolisation, boration / 3.2: Addition / 4.1: Substitution / 5.1: Substitution / 6.1: Reduction / 7.1: Oxidation / 8.1: deprotonation, Still-Horner olefination / 8.2: Condensation / 9.1: ether cleavage, lactonization / 10.1: Addition / 11.1: Hydrolysis / 12.1: Esterification / 13.1: Esterification;

DOI:10.1016/S0040-4020(00)00081-8

upstream raw materials:

Alloc-(S)-Ala-(S)-Me-Val-Gly-OH

(2E)-2,4,4-trimethylpent-2-en-1-ol

4,4-dimethyl-2-pentyne

(2E)-2,4,4-trimethylpent-2-enal