(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

Base Information

Chemical Name:(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester
CAS No.:182282-12-8
Molecular Formula:C₁₈H₂₈O₅
Molecular Weight:324.417
Hs Code.:

Synonyms:(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

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Chemical Property of (S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

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Technology Process of (S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

There total 26 articles about (S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl 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:

: 182282-00-4
(R)-1-((2S,3S)-3-Ethyl-3-hydroxymethyl-oxiranyl)-ethanol

: 182282-12-8
(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 20 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C 5 min and 1 h, room t.

2: CH₂Cl₂ / 12 h / Ambient temperature

3: BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

4: DIBAL-H / CH₂Cl₂ / 0.25 h / -20 °C

5: 99.6 percent / CSA / dimethylformamide / 0.25 h / 90 °C

6: 40 percent / H₂ / 10percent Pd/C

7: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 0 deg C and room t., 1 h

8: 1N HCl / methanol / 1 h / Ambient temperature

9: 83.3 percent / pyridine / 1 h / 90 °C

10: 98.3 percent / pyridine / 1.5 h / Ambient temperature

11: 93.2 percent / DBU / toluene / 30 h / Heating

12: 1.) BF₃*THF, 2.) NaOH, 30percent H₂O₂ / 1.) THF, room t., 19 h, 2.) THF, water, 2 h, room t.

13: 98.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.5 h / 0 °C

14: 82.1 percent / 80percent aq. AcOH / 1.5 h / 60 °C

15: DMSO, Et₃N, SO₃*Pyridine / CH₂Cl₂ / 0.33 h / Ambient temperature

16: NaClO₂, 2-Me-2-butene, NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol / 1 h / Ambient temperature

17: 80 percent / 1N HCl/MeOH / 1 h / 60 °C

18: 92.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 °C

19: 1.5N aq. KOH / methanol / 2.5 h / 80 °C

20: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/COM-96-7506

Reference yield:

: (E)-(R)-4-Ethyl-4-formyl-5-oxo-hex-2-enoic acid methyl ester

: 182282-12-8
(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: DIBAL-H / CH₂Cl₂ / 0.25 h / -20 °C

2: 99.6 percent / CSA / dimethylformamide / 0.25 h / 90 °C

3: 40 percent / H₂ / 10percent Pd/C

4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 0 deg C and room t., 1 h

5: 1N HCl / methanol / 1 h / Ambient temperature

6: 83.3 percent / pyridine / 1 h / 90 °C

7: 98.3 percent / pyridine / 1.5 h / Ambient temperature

8: 93.2 percent / DBU / toluene / 30 h / Heating

9: 1.) BF₃*THF, 2.) NaOH, 30percent H₂O₂ / 1.) THF, room t., 19 h, 2.) THF, water, 2 h, room t.

10: 98.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.5 h / 0 °C

11: 82.1 percent / 80percent aq. AcOH / 1.5 h / 60 °C

12: DMSO, Et₃N, SO₃*Pyridine / CH₂Cl₂ / 0.33 h / Ambient temperature

13: NaClO₂, 2-Me-2-butene, NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol / 1 h / Ambient temperature

14: 80 percent / 1N HCl/MeOH / 1 h / 60 °C

15: 92.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 °C

16: 1.5N aq. KOH / methanol / 2.5 h / 80 °C

17: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/COM-96-7506

Reference yield:

: 182281-94-3
(S,E)-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)butan-1-ol

: 182282-12-8
(S)-2-Ethyl-2-(2-hydroxy-ethyl)-5-methoxymethoxy-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 26 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, room t., 1 h

2: 97.7 percent / 80percent AcOH / 2 h / 80 °C

3: 68.3 percent / pyridine / 12 h / Ambient temperature

4: 97 percent / LAH / tetrahydrofuran; CH₂Cl₂ / 1 h / Ambient temperature

5: 93.8 percent / m-CPBA / CH₂Cl₂ / 1 h / 0 °C

6: 99 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol; H₂O; acetic acid / 1 h / Ambient temperature

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C 5 min and 1 h, room t.

8: CH₂Cl₂ / 12 h / Ambient temperature

9: BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -20 °C

10: DIBAL-H / CH₂Cl₂ / 0.25 h / -20 °C

11: 99.6 percent / CSA / dimethylformamide / 0.25 h / 90 °C

12: 40 percent / H₂ / 10percent Pd/C

13: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 0 deg C and room t., 1 h

14: 1N HCl / methanol / 1 h / Ambient temperature

15: 83.3 percent / pyridine / 1 h / 90 °C

16: 98.3 percent / pyridine / 1.5 h / Ambient temperature

17: 93.2 percent / DBU / toluene / 30 h / Heating

18: 1.) BF₃*THF, 2.) NaOH, 30percent H₂O₂ / 1.) THF, room t., 19 h, 2.) THF, water, 2 h, room t.

19: 98.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.5 h / 0 °C

20: 82.1 percent / 80percent aq. AcOH / 1.5 h / 60 °C

21: DMSO, Et₃N, SO₃*Pyridine / CH₂Cl₂ / 0.33 h / Ambient temperature

22: NaClO₂, 2-Me-2-butene, NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol / 1 h / Ambient temperature

23: 80 percent / 1N HCl/MeOH / 1 h / 60 °C

24: 92.7 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 °C

25: 1.5N aq. KOH / methanol / 2.5 h / 80 °C

26: K₂CO₃ / dimethylformamide / 1 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/COM-96-7506