(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

Base Information

Chemical Name:(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid
CAS No.:502506-87-8
Molecular Formula:C₂₇H₂₄Cl₄O₅
Molecular Weight:570.297
Hs Code.:

Synonyms:(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

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Chemical Property of (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

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Technology Process of (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

There total 8 articles about (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic 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: 81.0%

: 502506-84-5
(1R,3R,4S)-8-phenylmenthyl (2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoate

: 502506-87-8
(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

Guidance literature:: With potassium hydroxide; In 1,2-dimethoxyethane; ethanol; water; at 65 ℃; for 20h;
DOI:10.1016/S0040-4020(02)01451-5

Reference yield:

: 102-47-6
3,4-Dichlorophenylmethyl chloride

: 502506-87-8
(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 67 percent / K₂CO₃; KI / dimethylformamide / 10 h / Heating

2: 81 percent / SnCl₄ / CH₂Cl₂ / 22 h / -47 °C

3: 81 percent / KOH / ethanol; 1,2-dimethoxy-ethane; H₂O / 20 h / 65 °C

With potassium hydroxide; tin(IV) chloride; potassium carbonate; potassium iodide; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01451-5

Reference yield:

: 488-17-5
3-methylbenzene-1,2-diol

: 502506-87-8
(2S,3R)-3-[2,3-bis(3,4-dichlorobenzyloxy)-4-methylphenyl]-2-hydroxy-4-methylpent-4-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / NaH / dimethylformamide; methanol / 0.5 h / 0 °C

2.1: n-C₄H₉Li / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / 0 °C

3.1: n-C₄H₉Li / tetrahydrofuran; hexane / 1 h / 0 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

4.1: 99 percent / HCl / ethyl acetate / 0.75 h

5.1: 67 percent / K₂CO₃; KI / dimethylformamide / 10 h / Heating

6.1: 81 percent / SnCl₄ / CH₂Cl₂ / 22 h / -47 °C

7.1: 81 percent / KOH / ethanol; 1,2-dimethoxy-ethane; H₂O / 20 h / 65 °C

With hydrogenchloride; potassium hydroxide; n-butyllithium; tin(IV) chloride; sodium hydride; potassium carbonate; potassium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01451-5