diethyl (2S,3R)-3-hydroxy-2-methylsuccinate

Base Information

Chemical Name:diethyl (2S,3R)-3-hydroxy-2-methylsuccinate
CAS No.:74213-61-9
Molecular Formula:C₉H₁₆O₅
Molecular Weight:204.223
Hs Code.:

Synonyms:

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Chemical Property of diethyl (2S,3R)-3-hydroxy-2-methylsuccinate

Chemical Property:

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Technology Process of diethyl (2S,3R)-3-hydroxy-2-methylsuccinate

There total 2 articles about diethyl (2S,3R)-3-hydroxy-2-methylsuccinate 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:

: 759-65-9
diethyl oxalpropionate

: 73840-71-8,73840-72-9,74213-61-9,80951-78-6,93504-92-8,104420-20-4,107494-30-4
ethyl threo-2-hydroxy-3-methylbutane-1,4-dioate

: 73840-71-8,73840-72-9,74213-61-9,80951-78-6,93504-92-8,104420-20-4,107494-30-4
ethyl erythro-2-hydroxy-3-methylbutane-1,4-dioate

Guidance literature:: With sodium tetrahydroborate; further methyl 3-alkyl-2-oxobutane-1,4-dioates;

Reference yield:

: 759-65-9
diethyl oxalpropionate

: 73840-71-8,73840-72-9,74213-61-9,80951-78-6,93504-92-8,104420-20-4,107494-30-4
ethyl threo-2-hydroxy-3-methylbutane-1,4-dioate

: 73840-71-8,73840-72-9,74213-61-9,80951-78-6,93504-92-8,104420-20-4,107494-30-4
ethyl erythro-2-hydroxy-3-methylbutane-1,4-dioate

Guidance literature:: With sodium tetrahydroborate; further methyl 3-alkyl-2-oxobutane-1,4-dioates;

Reference yield:

: 74213-61-9
diethyl (2S,3R)-3-hydroxy-2-methylsuccinate

: (2S,3S)-3-<(2R,4R,5R)-5-Methyl-2-phenyl-1,3-dioxan-4-yl>-2-methoxybutane

Guidance literature:: Multi-step reaction with 17 steps

1: 10 M borane*dimethyl sulfide / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) reflux, 2.5 h

2: p-toluenesulfonic acid / dimethylformamide / 16 h / Ambient temperature

3: oxalyl chloride, DMSO, (iPr)2EtN / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) r.t., 1.5 h

4: CH₂Cl₂ / 2 h / Ambient temperature

5: 97 percent / 1 N aq. HCl / tetrahydrofuran / 18 h / 25 °C

6: NaHCO₃, I₂ / tetrahydrofuran / 18 h / 25 °C

7: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

8: 78 percent / Bu₃SnH, Et₃B / toluene / 0.5 h / -78 °C

9: 99 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2.5 h

10: 74 percent / N,N-diisopropylethylamine, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / 25 °C

11: 69 percent / NaH / dimethylformamide / 1.) 0 deg C, 20 min, 2.) 25 deg C, 18 h

12: tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 25 °C

13: 97 percent / pyridine / CH₂Cl₂ / 18 h / 25 °C

14: Et₃N, Me₂BBr / CH₂Cl₂ / 3 h

15: tributyltin hydride / AIBN / hexane / 1 h / Heating

16: 74 percent / 2 N aq. NaOH / methanol / 1.5 h / 25 °C

17: 90 percent / p-toluenesulfonic acid / CH₂Cl₂ / 18 h / 25 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; dimethylboron bromide; triethyl borane; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00084a040