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

Base Information

• Chemical Name: methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate
• CAS No.: 105631-38-7
• Molecular Formula: C₁₇H₂₈O₅
• Molecular Weight: 312.406
• Mol file: 105631-38-7.mol

Synonyms:

Chemical Property of methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate

There total 16 articles about methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate 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: 5.3%

methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate (105631-37-6) → methyl 3α-(3-ethylenedioxybutyl)-2,2,4α-trimethyl-5-oxocyclohexane-1α-carboxylate (105631-38-7,123886-86-2,123886-87-3) + 5-Hydroxy-2,2,4-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclohex-3-enecarboxylic acid methyl ester (123886-88-4,123887-16-1) + methyl 3α-(3-ethylenedioxybutyl)-5α-hydroxy-2,2,4α-trimethylcyclohexane-1α-carboxylate (105631-08-1,123932-48-9,123932-49-0) + methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate (105631-38-7,123886-86-2,123886-87-3)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In ethyl acetate; for 6h; under 73550.8 Torr; Ambient temperature;

DOI:10.1248/cpb.36.4722

Reference yield: 5.3%

methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate (105631-37-6) → methyl 3α-(3-ethylenedioxybutyl)-2,2,4α-trimethyl-5-oxocyclohexane-1α-carboxylate (105631-38-7,123886-86-2,123886-87-3) + 5-Hydroxy-2,2,4-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclohex-3-enecarboxylic acid methyl ester (123886-88-4,123887-16-1) + methyl 3α-(3-ethylenedioxybutyl)-5α-hydroxy-2,2,4α-trimethylcyclohexane-1α-carboxylate (105631-08-1,123932-48-9,123932-49-0) + methyl 3α-(3-ethylenedioxybutyl)-2,2,4β-trimethyl-5-oxocyclohexane-1α-carboxylate (105631-38-7,123886-86-2,123886-87-3)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In ethyl acetate; for 6h; under 73550.8 Torr; Ambient temperature;

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) → methyl 3α-(3-ethylenedioxybutyl)-2,2,4α-trimethyl-5-oxocyclohexane-1α-carboxylate (105631-38-7,123886-86-2,123886-87-3)

Guidance literature:

Multi-step reaction with 5 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

With jones reagent; titanium(III) chloride; Zeolite A-3; ammonium acetate; hydrogen; sodium methylate; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; water; ethyl acetate; acetone; benzene;

DOI:10.1248/cpb.36.4722

upstream raw materials:

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

2-ethylenedioxy-4-(2,6,6-trimethyl-5-nitromethyl-3-oxo-1-cyclohexen-1-yl)butane

2,2,4-trimethyl-5-oxo-3-(3-oxobutyl)cyclohexanecarboxylic acid

2,2,4-Trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-5-oxo-cyclohex-3-enecarbaldehyde

Downstream raw materials:

methyl 3α-(3-ethylenedioxybutyl)-5β-hydroxy-2,2,4α-trimethylcyclohexane-1α-carboxylate

methyl 3α-(3-ethylenedioxybutyl)-5α-hydroxy-2,2,4α-trimethylcyclohexane-1α-carboxylate

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

{(1S,5R)-4,6,6-Trimethyl-5-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclohex-3-enyl}-methanol

Refernces

• 1、 Ohtsuka,Oishi. "Studies on taxane synthesis. II. Syntheses of 3,8,11,11-tetramethyl-4-oxo- and 4,8,11,11-tetramethyl-3-oxo-bicyclo[5.3.1]undec-8-enes corresponding to the A- and B-rings of taxane diterpenes". . p. 4722 - 4736. Retrieved 2007/10/02.