Methanone, [(3S,4R,6R)-2-[[(3,4-dimethoxyphenyl)methoxy]methyl]-6-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-3-ethenyl-3,4-dimethyl-1-cyclohexen-1-yl][(2S,3R )-3-[(3E)-4-iodo-3-pentenyl]-3-methyloxiranyl]-

Base Information

• Chemical Name: Methanone, [(3S,4R,6R)-2-[[(3,4-dimethoxyphenyl)methoxy]methyl]-6-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-3-ethenyl-3,4-dimethyl-1-cyclohexen-1-yl][(2S,3R )-3-[(3E)-4-iodo-3-pentenyl]-3-methyloxiranyl]-
• CAS No.: 501369-25-1
• Molecular Formula: C35H53IO6Si
• Molecular Weight: 724.792

Synonyms:

Chemical Property of Methanone, [(3S,4R,6R)-2-[[(3,4-dimethoxyphenyl)methoxy]methyl]-6-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-3-ethenyl-3,4-dimethyl-1-cyclohexen-1-yl][(2S,3R )-3-[(3E)-4-iodo-3-pentenyl]-3-methyloxiranyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methanone, [(3S,4R,6R)-2-[[(3,4-dimethoxyphenyl)methoxy]methyl]-6-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-3-ethenyl-3,4-dimethyl-1-cyclohexen-1-yl][(2S,3R )-3-[(3E)-4-iodo-3-pentenyl]-3-methyloxiranyl]-

There total 29 articles about Methanone, [(3S,4R,6R)-2-[[(3,4-dimethoxyphenyl)methoxy]methyl]-6-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-3-ethenyl-3,4-dimethyl-1-cyclohexen-1-yl][(2S,3R )-3-[(3E)-4-iodo-3-pentenyl]-3-methyloxiranyl]- 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: 90.0%

[(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2R,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanol (501369-44-4) → [(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone (501369-25-1)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ja0296531

Reference yield:

pulegone (89-82-7,90449-51-7) → [(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone (501369-25-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 70 percent / LDA; LiCl

2.1: 75 percent / KOH / Heating

3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

5.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

5.2: diethyl ether; petroleum ether / 1 h / -78 °C

6.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

7.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

7.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

7.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

8.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

9.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

10.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

11.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

12.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

13.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

14.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

14.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

15.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

16.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C

16.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

17.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C

18.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

18.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C

19.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; tert.-butyl lithium; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; 4-nitro-benzoic acid; chloro-trimethyl-silane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; pentane; 16.1: Mitsunobu inversion;

DOI:10.1021/ja0296531

Reference yield:

(2RS,3R)-2,3-dimethylcyclohexanone (234078-11-6) → [(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone (501369-25-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

1.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

2.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

3.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

3.2: diethyl ether; petroleum ether / 1 h / -78 °C

4.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

5.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

5.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

5.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

6.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

7.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

8.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

9.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

10.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

11.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

12.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

12.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

13.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

14.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C

14.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

15.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C

16.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

16.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C

17.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; tert.-butyl lithium; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; diethylazodicarboxylate; 4-nitro-benzoic acid; chloro-trimethyl-silane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; pentane; 14.1: Mitsunobu inversion;

DOI:10.1021/ja0296531

upstream raw materials:

[(3S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2R,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanol

(3R)-6-bromo-2,3-dimethylcyclohexanone

(4S,5R)-2-bromo-3-methoxymethoxymethyl-4,5-dimethyl-4-vinylcyclohex-2-enone

(2R,3R,6E)-[3-(4-iodo-pent-3-enyl)-3-methyloxiranyl]-methanol

Downstream raw materials:

[(3S,4R,6R)-2-(3,4-Dimethoxy-benzyloxymethyl)-6-hydroxy-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone

(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-3-triethylsilanyloxy-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

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