(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

Base Information

Chemical Name:(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate
CAS No.:373392-36-0
Molecular Formula:C₃₁H₄₀O₄
Molecular Weight:476.656
Hs Code.:

Synonyms:(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

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Chemical Property of (1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

Chemical Property:

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Technology Process of (1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

There total 4 articles about (1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate 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:

: 85664-76-2
2-<(2,2-dimethylpropanoyl)oxy>-2-phenylethanone

: (Bis-o-tolyloxy-phosphoryl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

: (1'R,2'S,5'R)-8'-phenylmenthyl (2Z,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

: 373392-18-8
(1'R,2'S,5'R)-8'-phenylmenthyl (2Z,4R)-4-phenyl-4-pivaloyloxy-2-butenoate

: 373392-36-0
(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

: (1'R,2'S,5'R)-8'-phenylmenthyl (2E,4R)-4-phenyl-4-pivaloyloxy-2-butenoate

Guidance literature:: (Bis-o-tolyloxy-phosphoryl)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

2-<(2,2-dimethylpropanoyl)oxy>-2-phenylethanone; In tetrahydrofuran; at -78 ℃; for 3h; Further stages.;
DOI:10.1021/ja005809q

Reference yield:

: 4393-06-0
1-Phenyl-2-propen-1-ol

: 373392-36-0
(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / DMAP; pyridine / CH₂Cl₂ / 16 h / Heating

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: 73 percent / Me₂S / CH₂Cl₂; methanol / 3 h / 20 °C

3.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 3 h / -78 °C

With pyridine; dmap; 18-crown-6 ether; potassium hexamethylsilazane; ozone; In tetrahydrofuran; methanol; dichloromethane; 3.2: asymmetric Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja005809q

Reference yield:

: 3282-30-2
pivaloyl chloride

: 373392-36-0
(1'R,2'S,5'R)-8'-phenylmenthyl (2E,4S)-4-phenyl-4-pivaloyloxy-2-butenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / DMAP; pyridine / CH₂Cl₂ / 16 h / Heating

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: 73 percent / Me₂S / CH₂Cl₂; methanol / 3 h / 20 °C

3.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 3 h / -78 °C

With pyridine; dmap; 18-crown-6 ether; potassium hexamethylsilazane; ozone; In tetrahydrofuran; methanol; dichloromethane; 3.2: asymmetric Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ja005809q