(3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Base Information

• Chemical Name: (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one
• CAS No.: 1026853-78-0
• Molecular Formula: C₄₀H₅₄O₈
• Molecular Weight: 662.864

Synonyms:(3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Chemical Property of (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one

There total 37 articles about (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one 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:

(S)-4-Methyl-1-(tetrahydro-pyran-2-yloxy)-pent-4-en-2-ol (289472-93-1) → (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one (1026853-78-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / KH; 18-crown-6 / tetrahydrofuran / 0 - 23 °C

2.1: Cl₂(PCy₃₀₂Ru=CHPh / CH₂Cl₂ / 2 h / 23 °C

3.1: 3.96 g / CSA / methanol / 1 h

4.1: 85 percent / DMSO; (COCl)2; iPr₂NEt / CH₂Cl₂ / -78 - 23 °C

5.1: 67 percent / PPh₃ / CH₂Cl₂ / 0 - 23 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

6.2: 64 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

8.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

9.1: 81 percent / Red-Al / tetrahydrofuran / -40 - -20 °C

10.1: TFA / CH₂Cl₂ / 1 h / 23 °C

11.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

12.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

13.1: 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt; DMAP / tetrahydrofuran; benzene / 23 °C

14.1: 32 mg / AcOH / tetrahydrofuran; H₂O / 3 h / 23 °C

15.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

16.1: 10 mg / K₂CO₃; 18-crown-6 / toluene / -20 - 0 °C

With dmap; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium hydride; L-Selectride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; benzene; 4.1: Swern oxidation / 17.1: Horner-Emmons reaction;

DOI:10.1021/jo010854h

Reference yield:

(2S)-2-(2-allyloxy-4-methyl-pent-4-enyloxy)-tetrahydropyran (289472-94-2) → (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one (1026853-78-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Cl₂(PCy₃₀₂Ru=CHPh / CH₂Cl₂ / 2 h / 23 °C

2.1: 3.96 g / CSA / methanol / 1 h

3.1: 85 percent / DMSO; (COCl)2; iPr₂NEt / CH₂Cl₂ / -78 - 23 °C

4.1: 67 percent / PPh₃ / CH₂Cl₂ / 0 - 23 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

5.2: 64 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

7.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

8.1: 81 percent / Red-Al / tetrahydrofuran / -40 - -20 °C

9.1: TFA / CH₂Cl₂ / 1 h / 23 °C

10.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

11.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

12.1: 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt; DMAP / tetrahydrofuran; benzene / 23 °C

13.1: 32 mg / AcOH / tetrahydrofuran; H₂O / 3 h / 23 °C

14.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

15.1: 10 mg / K₂CO₃; 18-crown-6 / toluene / -20 - 0 °C

With dmap; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; L-Selectride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; benzene; 3.1: Swern oxidation / 16.1: Horner-Emmons reaction;

DOI:10.1021/jo010854h

Reference yield:

[3R]-4-Benzyloxy-3-methylbutanal (90865-70-6) → (3E,9E)-(1R,7S,11S,15S,17R)-7-[(E)-(S)-1-(4-Methoxy-benzyloxy)-3-((R)-4-methyl-5,6-dihydro-2H-pyran-2-yl)-allyl]-11-methoxymethoxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one (1026853-78-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: tetrahydrofuran; hexane / 0.5 h / -100 °C

2.1: 83 percent / PPTS / benzene / 12 h

3.1: Cl₂(PCy₃)2Ru=CHPh / benzene / 12 h

3.2: 4.11 g / Montmorillonite K-10 / CH₂Cl₂ / 0.5 h / 23 °C

4.1: 54 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 75 percent / imidazole / dimethylformamide / 3 h / 23 °C

6.1: 95 percent / Li; liquid NH₃ / tetrahydrofuran / 0.17 h

7.1: 96 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 0.5 h / 0 °C

8.1: NaH / dimethylformamide; various solvent(s) / 0.25 h / 0 °C

8.2: 89 percent / dimethylformamide / 12 h / 60 °C

9.1: Red-Al / tetrahydrofuran / 0.17 h / 0 °C

10.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 23 °C

11.1: 3.61 g / sodium amalgam; Na₂HPO₄ / methanol / -20 - 23 °C

12.1: i-Pr₂NEt / CH₂Cl₂ / 3 h / 23 °C

13.1: 2.5 g / DDQ / CH₂Cl₂; various solvent(s) / 2 h / 23 °C / pH 7

14.1: 85 percent / DMSO; (COCl)2; i-Pr₂NEt / CH₂Cl₂ / -78 °C

15.1: 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt; DMAP / tetrahydrofuran; benzene / 23 °C

16.1: 32 mg / AcOH / tetrahydrofuran; H₂O / 3 h / 23 °C

17.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

18.1: 10 mg / K₂CO₃; 18-crown-6 / toluene / -20 - 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; oxalyl dichloride; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; ammonia; iodine; lithium; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 14.1: Swern oxidation / 19.1: Horner-Emmons reaction;

DOI:10.1021/jo010854h

upstream raw materials:

[bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-7-{2-methyl-3-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propyl}-octa-3,7-dienyl ester

[(2R,4S)-4-(1-Ethoxy-allyloxy)-2-methyl-hept-6-enyloxymethyl]-benzene

[3R]-4-Benzyloxy-3-methylbutanal

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

Downstream raw materials:

laulimalide

(Z)-(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[(E)-(S)-1-(4-methoxy-benzyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docosa-15,19-dien-14-one

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