(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

Base Information

Chemical Name:(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid
CAS No.:313255-19-5
Molecular Formula:C₁₉H₃₅NO₄
Molecular Weight:341.491
Hs Code.:

Synonyms:(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

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Chemical Property of (2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

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Technology Process of (2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

There total 7 articles about (2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic 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:

: 313255-17-3
(3R,4S)-1-(2-tetrahydro-2H-pyran-2-yloxy)-3-(4-methylcyclohexylmethyl)-4-isopropylazetidin-2-one

: 313255-19-5
(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

Guidance literature:: With sodium hydroxide; In 1,4-dioxane; at 40 ℃; for 24h;
DOI:10.1021/jm0102654

Reference yield:

: 65596-31-8,76835-65-9,114489-57-5,110097-32-0
methyl (S)-3-hydroxy-4-methylvalerate

: 313255-19-5
(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: LDA; DMPU / tetrahydrofuran / -78 - 0 °C

2: 70 percent / H₂ / Rh/Al₂O₃ / methanol / 3620.13 Torr

3: aq. LiOH / tetrahydrofuran; methanol / 24 h

4: DCC / ethyl acetate / 0 - 20 °C

5: pyridine / CH₂Cl₂ / 0 °C

6: K₂CO₃ / acetone / 12 h / Heating

7: aq. NaOH / dioxane / 24 h / 40 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; sodium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; lithium diisopropyl amide; Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; acetone; 1: Frater-Seebach alkylation;
DOI:10.1021/jm0102654

Reference yield:

: 313219-57-7
methyl (2R,3R)-3-hydroxy-4-methyl-2-(4-methylbenzyl)pentanoate

: 313255-19-5
(2R,3S)-4-Methyl-2-(4-methyl-cyclohexylmethyl)-3-(tetrahydro-pyran-2-yloxyamino)-pentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / H₂ / Rh/Al₂O₃ / methanol / 3620.13 Torr

2: aq. LiOH / tetrahydrofuran; methanol / 24 h

3: DCC / ethyl acetate / 0 - 20 °C

4: pyridine / CH₂Cl₂ / 0 °C

5: K₂CO₃ / acetone / 12 h / Heating

6: aq. NaOH / dioxane / 24 h / 40 °C

With pyridine; lithium hydroxide; sodium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; Rh/Al₂O₃; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; acetone;
DOI:10.1021/jm0102654