2-methyl-3-pentanol (R)-(+)-MTPA ester

Base Information

• Chemical Name: 2-methyl-3-pentanol (R)-(+)-MTPA ester
• CAS No.: 86535-19-5
• Molecular Formula: C₁₆H₂₁F₃O₃
• Molecular Weight: 318.336
• Mol file: 86535-19-5.mol

Synonyms:2-methyl-3-pentanol (R)-(+)-MTPA ester

Chemical Property of 2-methyl-3-pentanol (R)-(+)-MTPA ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-3-pentanol (R)-(+)-MTPA ester

There total 31 articles about 2-methyl-3-pentanol (R)-(+)-MTPA ester 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:

D,L-threo-β-methylaspartic acid (642-92-2,1114-07-4,2955-50-2,4846-45-1,5941-19-5,6061-13-8,6667-60-3,7298-96-6,31571-69-4,86562-29-0,121570-10-3,127001-58-5) → 2-methyl-3-pentanol (R)-(+)-MTPA ester (86535-19-5)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) acetone, MeOH, water; 2.) water, HCl, pH=3, EtOH

2: NaNO₂ / H₂O; H₂SO₄ / 0 - 25 °C

3: diethyl ether

4: p-TsOH / diethyl ether / Ambient temperature

5: LAH / diethyl ether

6: p-TsOH / methanol / Ambient temperature

7: p-TsOH / Ambient temperature

8: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

9: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

10: 92 percent / pyridine / 0 - 5 °C

11: 66 percent / KOH / methanol / 0.58 h / 0 - 17 °C

12: 82 percent / CuI / diethyl ether / -55 - -20 °C

13: 98 percent / p-TsOH / diethyl ether / Ambient temperature

14: 88 percent / H₂ / Pd-C (5percent) / ethanol

15: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

16: p-TsOH / methanol / Ambient temperature

17: LAH / diethyl ether / 12 h / Heating

With 3,4-dihydro-2H-pyran; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; toluene-4-sulfonic acid; sodium nitrite; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; sulfuric acid; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(82)80081-1

Reference yield:

(2S,3S)-dimethyl threo-3-methylmalate THP ether (78433-53-1) → 2-methyl-3-pentanol (R)-(+)-MTPA ester (86535-19-5)

Guidance literature:

Multi-step reaction with 14 steps

1: LAH / diethyl ether

2: p-TsOH / methanol / Ambient temperature

3: p-TsOH / Ambient temperature

4: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

5: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

6: 92 percent / pyridine / 0 - 5 °C

7: 66 percent / KOH / methanol / 0.58 h / 0 - 17 °C

8: 82 percent / CuI / diethyl ether / -55 - -20 °C

9: 98 percent / p-TsOH / diethyl ether / Ambient temperature

10: 88 percent / H₂ / Pd-C (5percent) / ethanol

11: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

12: p-TsOH / methanol / Ambient temperature

13: LAH / diethyl ether / 12 h / Heating

With 3,4-dihydro-2H-pyran; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(82)80081-1

Reference yield:

(2S,3R)-threo-3-methylbutane-1,2,4-triol (77333-42-7) → 2-methyl-3-pentanol (R)-(+)-MTPA ester (86535-19-5)

Guidance literature:

Multi-step reaction with 12 steps

1: p-TsOH / Ambient temperature

2: NaCH₂SOMe / dimethylsulfoxide / 5 h / Ambient temperature

3: aq. HCl; methanol; H₂O / 6.5 h / 60 °C

4: 92 percent / pyridine / 0 - 5 °C

5: 66 percent / KOH / methanol / 0.58 h / 0 - 17 °C

6: 82 percent / CuI / diethyl ether / -55 - -20 °C

7: 98 percent / p-TsOH / diethyl ether / Ambient temperature

8: 88 percent / H₂ / Pd-C (5percent) / ethanol

9: 2.) p-TsOH, dihydropyran / 1.) C₅H₅N, 8 h; 2.) ether, room temp.

10: p-TsOH / methanol / Ambient temperature

11: LAH / diethyl ether / 12 h / Heating

With 3,4-dihydro-2H-pyran; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(82)80081-1

upstream raw materials:

(+)-(R)-2-methyl-3-pentanol

(S)-Mosher acid

(S)-2-methyl-3-pentanol

(2S,3S)-3-methylaspartic acid