(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

Base Information

• Chemical Name: (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester
• CAS No.: 110881-04-4
• Molecular Formula: C₅₁H₈₀O₁₃
• Molecular Weight: 901.188
• Mol file: 110881-04-4.mol

Synonyms:(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

Chemical Property of (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

There total 14 articles about (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester 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: 94.0%

O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester (105238-82-2,111001-55-9) → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester (110881-04-4)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 1.5h; Ambient temperature;

DOI:10.1055/s-1986-31846

Reference yield:

(furan-2-yl)ethylene (1487-18-9) → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester (110881-04-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) m-tolyl-lithium / 2.) THF, 5 deg C, 4 h, to room temp.

2: 0.5 h

3: 90 percent / TPP, H₂ / 2 / 24 h / 70 °C / 76000 Torr

4: NaClO₂, H₂N-SO₃H, Na₂HPO₄ / dioxane; H₂O / 0.5 h / Ambient temperature

5: KOH / methanol / 0.5 h / Ambient temperature

6: diethyl ether / 0.03 h / Ambient temperature

7: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

8: KOH / methanol / 0.5 h / Ambient temperature

9: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

10: 96 percent / imidazole / dimethylformamide / 1 h / 50 °C

11: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

12: Me₂C=C(Cl)NMe₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

13: 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

14: 94 percent / 40percent aq. HF / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; aminosulfonic acid; hydrogen fluoride; hydrogen; thiamine diphosphate; m-tolyllithium; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; palladium on activated charcoal; Rh/Al₂O₃; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c39860000996

Reference yield:

5-<(2S)-Hydroxybutyl>-α(R,S)-methylfuran-2-essigsaeure-methylester (105210-94-4,105210-95-5) → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester (110881-04-4)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

2: KOH / methanol / 0.5 h / Ambient temperature

3: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

4: 96 percent / imidazole / dimethylformamide / 1 h / 50 °C

5: H₂ / 5percent Pd/C / tetrahydrofuran / 1 h / Ambient temperature

6: Me₂C=C(Cl)NMe₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

7: 4-pyrrolidinopyridine / CH₂Cl₂ / 2 h / Ambient temperature

8: 94 percent / 40percent aq. HF / acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydrogen fluoride; hydrogen; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c39860000996

upstream raw materials:

O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

(furan-2-yl)ethylene

2-<2(S)-Acetoxybutyl>-5-vinylfuran

5-<(2S)-Hydroxybutyl>-α(R,S)-methylfuran-2-essigsaeure-methylester

Downstream raw materials:

Tetranactin