4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid

Base Information

• Chemical Name: 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid
• CAS No.: 123887-14-9
• Molecular Formula: C₁₆H₂₈O₅S
• Molecular Weight: 332.461

Synonyms:

Chemical Property of 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid

There total 13 articles about 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid 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:

methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate (105631-37-6) → 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid (123887-14-9,123932-55-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

2: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

3: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

4: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

5: 1.94 g / pyridine / 1 h / Ambient temperature

6: p-TsOH / acetone / 2.5 h / Ambient temperature

7: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

8: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

9: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; hydrogen; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethyl acetate; acetone;

DOI:10.1248/cpb.36.4722

Reference yield:

2-ethylenedioxy-4-(2,6,6-trimethyl-5-nitromethyl-3-oxo-1-cyclohexen-1-yl)butane (105631-36-5) → 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid (123887-14-9,123932-55-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 88.4 percent / aq. 16percent titanium trichloride, AcONH₄, MeONa / H₂O; methanol / 0.33 h / Ambient temperature

2: 85.5 percent / Jones reagent / acetone / 0.5 h / 5 °C

3: 470 mg / K₂CO₃ / acetone / Heating

4: p-toluenesulfonic acid, Zeolite A-3 / benzene / 1 h / Heating

5: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

6: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

7: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

8: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

9: 1.94 g / pyridine / 1 h / Ambient temperature

10: p-TsOH / acetone / 2.5 h / Ambient temperature

11: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

12: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

13: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; titanium(III) chloride; Zeolite A-3; ammonium acetate; hydrogen; sodium methylate; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; ethyl acetate; acetone; benzene;

DOI:10.1248/cpb.36.4722

Reference yield:

2,2,4-trimethyl-5-oxo-3-(3-oxobutyl)cyclohexanecarboxylic acid (123886-83-9) → 4-((1R,5S)-5-Methanesulfonyloxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-2-methyl-butyric acid (123887-14-9,123932-55-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 470 mg / K₂CO₃ / acetone / Heating

2: p-toluenesulfonic acid, Zeolite A-3 / benzene / 1 h / Heating

3: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

4: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

5: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

6: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

7: 1.94 g / pyridine / 1 h / Ambient temperature

8: p-TsOH / acetone / 2.5 h / Ambient temperature

9: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

10: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

11: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; Zeolite A-3; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethyl acetate; acetone; benzene;

DOI:10.1248/cpb.36.4722

upstream raw materials:

methanesulfonyl chloride

4-(5α-acetoxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)-2-methylbutanoic acid

methyl 3α-(3-ethylenedioxybutyl)-2,2,4α-trimethyl-5-oxocyclohexane-1α-carboxylate

methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate

Downstream raw materials:

Methanesulfonic acid (1S,5R)-5-(3-chlorocarbonyl-butyl)-4,6,6-trimethyl-cyclohex-3-enylmethyl ester

4,8,11,11-tetramethyl-2-(2-methylamino)phenyllsulfinyl-3-oxobicyclo<5.3.1>undec-8-ene

N-methyl-2'-<(2-cyanoethyl)thio>-4-(5α-methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)-2-methylbutananilide

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