acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester

Base Information

• Chemical Name: acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester
• CAS No.: 476003-50-6
• Molecular Formula: C₃₁H₄₀O₇S
• Molecular Weight: 556.72

Synonyms:acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester

Chemical Property of acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester

There total 20 articles about acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl 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: 96.0%

acetic anhydride (108-24-7) + 4-benzenesulfonyl-1-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-4,8-dimethyl-non-7-en-3-ol (476003-49-3) → acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester (476003-50-6)

Guidance literature:

With pyridine; at 40 ℃; for 12h;

DOI:10.1271/bbb.66.1915

Reference yield:

hydroquinone monomethoxymethyl ether (57433-93-9) → acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester (476003-50-6)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 85 percent / K₂CO₃ / acetone / 10 h / Heating

2.1: 88 percent / N,N-diethylaniline / 5 h / 220 °C

3.1: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: 98 percent / 4-methylmorpholine-4-oxide; aq. OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: NaIO₄ / methanol; H₂O / 1 h / 20 °C

6.1: 98 percent / CH₂Cl₂ / 0 - 20 °C

7.1: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 - 20 °C

8.1: D-(-)-diethyl tartrate; tert-butylhydroperoxide; titanium tetraisopropoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

9.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1.25 h / -78 - -45 °C

10.1: 83 percent / CH₂Cl₂ / 0 - 20 °C

11.1: TBAF; AcOH / tetrahydrofuran / 0.05 h / 20 °C

12.1: 83 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

13.1: 92 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

14.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

15.1: 48.5 mg / DBU / xylene / 10 h / Heating

16.1: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

17.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 20 °C

18.1: n-BuLi / hexane; tetrahydrofuran / 0.17 h / -78 °C

18.2: 81 percent / hexane; tetrahydrofuran / 0.58 h / -78 - 20 °C

19.1: 96 percent / pyridine / 12 h / 40 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N,N-diethylaniline; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; xylene; 6.1: Wittig reaction / 8.1: Sharpless epoxydation / 9.1: Swern oxidation / 10.1: Wittig olefination / 18.1: Julia reaction / 18.2: Julia reaction;

DOI:10.1271/bbb.66.1915

Reference yield:

hydroquinone (123-31-9,8027-02-9) → acetic acid 2-benzenesulfonyl-1-[2-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-ethyl]-2,6-dimethyl-hept-5-enyl ester (476003-50-6)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 65 percent / N,N-diisopropylethylamine / acetonitrile / 0 - 20 °C

2.1: 85 percent / K₂CO₃ / acetone / 10 h / Heating

3.1: 88 percent / N,N-diethylaniline / 5 h / 220 °C

4.1: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 98 percent / 4-methylmorpholine-4-oxide; aq. OsO₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

6.1: NaIO₄ / methanol; H₂O / 1 h / 20 °C

7.1: 98 percent / CH₂Cl₂ / 0 - 20 °C

8.1: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 - 20 °C

9.1: D-(-)-diethyl tartrate; tert-butylhydroperoxide; titanium tetraisopropoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / -20 °C

10.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1.25 h / -78 - -45 °C

11.1: 83 percent / CH₂Cl₂ / 0 - 20 °C

12.1: TBAF; AcOH / tetrahydrofuran / 0.05 h / 20 °C

13.1: 83 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 6 h / 20 °C

14.1: 92 percent / H₂ / Pd/C / methanol / 10 h / 20 °C

15.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

16.1: 48.5 mg / DBU / xylene / 10 h / Heating

17.1: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

18.1: Dess-Martin reagent / CH₂Cl₂ / 3 h / 20 °C

19.1: n-BuLi / hexane; tetrahydrofuran / 0.17 h / -78 °C

19.2: 81 percent / hexane; tetrahydrofuran / 0.58 h / -78 - 20 °C

20.1: 96 percent / pyridine / 12 h / 40 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-diethylaniline; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; xylene; 7.1: Wittig reaction / 9.1: Sharpless epoxydation / 10.1: Swern oxidation / 11.1: Wittig olefination / 19.1: Julia reaction / 19.2: Julia reaction;

DOI:10.1271/bbb.66.1915

upstream raw materials:

acetic anhydride

4-benzenesulfonyl-1-(6-methoxymethoxy-2-methyl-2H-chromen-2-yl)-4,8-dimethyl-non-7-en-3-ol

hydroquinone monomethoxymethyl ether

hydroquinone

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