Product Name

  • Name

    (R)-2-METHYLSUCCINIC ACID 4-TERT-BUTYL ESTER

  • EINECS 208-224-2
  • CAS No. 185836-75-3
  • Article Data8
  • CAS DataBase
  • Density 1.072 g/cm3
  • Solubility
  • Melting Point 59-60℃
  • Formula C9H16O4
  • Boiling Point 281.928 °C at 760 mmHg
  • Molecular Weight 188.224
  • Flash Point 104.694 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 185836-75-3 ((R)-2-METHYLSUCCINIC ACID 4-TERT-BUTYL ESTER)
  • Hazard Symbols
  • Synonyms Butanedioic acid,methyl-, 4-(1,1-dimethylethyl) ester, (R)-;Butanedioicacid, methyl-, 4-(1,1-dimethylethyl) ester, (2R)- (9CI);
  • PSA 63.60000
  • LogP 1.43890

Synthetic route

(4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one
202874-73-5

(4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 0℃; for 2h; Hydrolysis;95%
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0℃; for 2h;88%
(S)-3-((R)-3-tert-Butoxycarbonyl-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
195829-02-8

(S)-3-((R)-3-tert-Butoxycarbonyl-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water for 3h; Ambient temperature;79%
(4R,2'R)-3-(4'-tert-butoxy-4'-oxo-2'-methylbutanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one
908290-81-3

(4R,2'R)-3-(4'-tert-butoxy-4'-oxo-2'-methylbutanoyl)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one

A

(R)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one
908290-56-2

(R)-4-iso-propyl-6,6-dimethyl-(1,3)-oxazinan-2-one

B

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 16h;A 16 mg
B 68%
2-(RS)-methyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
82701-21-1

2-(RS)-methyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester

A

(S)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid
182007-75-6

(S)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid

B

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide; Alcalase In acetone for 18h; Hydrolysis; Title compound not separated from byproducts;
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C
1.2: 74 percent / tetrahydrofuran; toluene / 2 h / -78 °C
2.1: 68 percent / aq. H2O2; LiOH / tetrahydrofuran / 16 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 84 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / -78 °C
2: 95 percent / H2O2; LiOH / tetrahydrofuran; H2O / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
1.2: 2.5 h / -78 °C
2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 °C
View Scheme
2-methoxycarbonyl-2-methyl-succinic acid 4-tert-butyl ester 1-methyl ester
144843-09-4

2-methoxycarbonyl-2-methyl-succinic acid 4-tert-butyl ester 1-methyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 33 percent / aq. lithium bromide / dimethylformamide / 8 h / 135 °C
2: alcalase; aq. NaOH / acetone / 18 h
View Scheme
2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid dibenzyl ester
170704-11-7

2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid dibenzyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / H2 / Pd/C / methanol / 3 h / Ambient temperature
2: 86 percent / dimethylsulfoxide / 1 h / 100 °C
3: 91 percent / H2SO4 / CH2Cl2 / 12 h / Ambient temperature
4: 79 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / Ambient temperature
View Scheme
(S)-3-((R)-3-Carboxy-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
195828-95-6

(S)-3-((R)-3-Carboxy-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / H2SO4 / CH2Cl2 / 12 h / Ambient temperature
2: 79 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / Ambient temperature
View Scheme
2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid
195828-92-3

2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / dimethylsulfoxide / 1 h / 100 °C
2: 91 percent / H2SO4 / CH2Cl2 / 12 h / Ambient temperature
3: 79 percent / LiOH*H2O / tetrahydrofuran; H2O / 3 h / Ambient temperature
View Scheme
potassium tert-butylate
865-47-4

potassium tert-butylate

(R)-2-methyl-succinic acid 4-methyl ester
23268-03-3, 80986-16-9, 111266-27-4, 81025-83-4

(R)-2-methyl-succinic acid 4-methyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With sulfuric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; water; tert-butyl alcohol
(R)-2-methyl-succinic acid 4-methyl ester
23268-03-3, 80986-16-9, 111266-27-4, 81025-83-4

(R)-2-methyl-succinic acid 4-methyl ester

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

aqueous sodium metabisulphite

aqueous sodium metabisulphite

(4S)-3-[(2R)-3-tert-butoxycarbonyl-2-methylpropionyl ]-4-isopropyloxazolidin-2-one

(4S)-3-[(2R)-3-tert-butoxycarbonyl-2-methylpropionyl ]-4-isopropyloxazolidin-2-one

citric acid
77-92-9

citric acid

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water
...Expand
N-benzyl-N-methoxyamine
20056-98-8

N-benzyl-N-methoxyamine

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

C17H25NO4

C17H25NO4

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Mechanism; Inert atmosphere;99%
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(R)-tert-butyl 4-hydroxy-3-methylbutanoate
185836-76-4

(R)-tert-butyl 4-hydroxy-3-methylbutanoate

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 24h; Reduction;97%
With borane-THF In tetrahydrofuran at 20℃;85%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃;
(S)-10-amino-2,3,5,10-tetrahydro-1H,11H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-11-one hydrochloride

(S)-10-amino-2,3,5,10-tetrahydro-1H,11H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-11-one hydrochloride

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl (R)-3-methyl-4-oxo-4-(((S)-11-oxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)butanoate

tert-butyl (R)-3-methyl-4-oxo-4-(((S)-11-oxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)butanoate

Conditions
ConditionsYield
With O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;95%
(S)-10-amino-6-fluoro-2,3,5,10-tetrahydro-1H,11H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-11-one hydrochloride

(S)-10-amino-6-fluoro-2,3,5,10-tetrahydro-1H,11H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-11-one hydrochloride

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl (R)-4-(((S)-6-fluoro-11-oxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)-3-methyl-4-oxobutanoate

tert-butyl (R)-4-(((S)-6-fluoro-11-oxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)-3-methyl-4-oxobutanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine at 20℃; for 4h;80%
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

benzyl alcohol
100-51-6

benzyl alcohol

tert-butyl (3R)-3-{[(benzyloxy)carbonyl]amino}butanoate

tert-butyl (3R)-3-{[(benzyloxy)carbonyl]amino}butanoate

Conditions
ConditionsYield
With diphenyl-phosphinic acid; triethylamine In toluene for 22h; Rearrangement; Curtius rearrangement; Heating;76%
With diphenyl-phosphinic acid; triethylamine 1.) toluene, 80 deg C, 1 h, 2.) 80 deg C, 14 h; Yield given. Multistep reaction;
(S)-10-amino-2,3-dihydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepine-5,11(10H)-dione hydrochloride

(S)-10-amino-2,3-dihydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepine-5,11(10H)-dione hydrochloride

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl (R)-4-(((S)-5,11-dioxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)-3-methyl-4-oxobutanoate

tert-butyl (R)-4-(((S)-5,11-dioxo-2,3,10,11-tetrahydro-1H,5H-benzo[d]pyrazolo[1,2-a][1,2]diazepin-10-yl)amino)-3-methyl-4-oxobutanoate

Conditions
ConditionsYield
With O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h;64%
(S)-N-(3-cyclopropyl-2-(methylamino)propyl)-4-nitrobenzenesulfonamide

(S)-N-(3-cyclopropyl-2-(methylamino)propyl)-4-nitrobenzenesulfonamide

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl (R)-4-(((S)-1-cyclopropyl-3-((4-nitrophenyl)sulfonamido)propan-2-yl)(methyl)amino)-3-methyl-4-oxobutanoate

tert-butyl (R)-4-(((S)-1-cyclopropyl-3-((4-nitrophenyl)sulfonamido)propan-2-yl)(methyl)amino)-3-methyl-4-oxobutanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;48%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

pivalaldehyde
630-19-3

pivalaldehyde

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(R)-N-(1-tert-Butylcarbamoyl-2,2-dimethyl-propyl)-3-methyl-succinamic acid tert-butyl ester

(R)-N-(1-tert-Butylcarbamoyl-2,2-dimethyl-propyl)-3-methyl-succinamic acid tert-butyl ester

Conditions
ConditionsYield
With ammonia In methanol Ambient temperature;
...Expand
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(R)-4-Methoxymethoxy-2-methyl-butan-1-ol
881018-08-2

(R)-4-Methoxymethoxy-2-methyl-butan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl-(4-methoxymethoxy-2-methyl-butoxy)-dimethyl-silane

tert-butyl-(4-methoxymethoxy-2-methyl-butoxy)-dimethyl-silane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

2-((R)-4-Methoxymethoxy-2-methyl-butylsulfanyl)-benzothiazole

2-((R)-4-Methoxymethoxy-2-methyl-butylsulfanyl)-benzothiazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

2-((R)-4-Methoxymethoxy-2-methyl-butane-1-sulfonyl)-benzothiazole
881017-96-5

2-((R)-4-Methoxymethoxy-2-methyl-butane-1-sulfonyl)-benzothiazole

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(2R,3S,4aR,8S,10aS)-3-Methoxy-2-methoxymethyl-8,10a-dimethyl-octahydro-1,5-dioxa-benzocycloocten-6-one

(2R,3S,4aR,8S,10aS)-3-Methoxy-2-methoxymethyl-8,10a-dimethyl-octahydro-1,5-dioxa-benzocycloocten-6-one

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: BH3*Me2S / tetrahydrofuran / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 °C
3.1: LiAlH4 / tetrahydrofuran / 0 °C
4.1: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5.1: TBAF / tetrahydrofuran / 20 °C
6.1: DEAD; PPh3 / tetrahydrofuran / 20 °C
7.1: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8.1: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9.1: 39 percent / aq. HCl / methanol / 20 °C
10.1: H2 / PtO2 / methanol / 50 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: CSA / methanol / 20 °C
13.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
13.2: Et3N / -78 - 20 °C
14.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C
15.1: TBAF / tetrahydrofuran / 20 °C
16.1: Et3N / tetrahydrofuran / 0 °C
17.1: DMAP / benzene / 80 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(2S,3R,5S,6R)-2-((E)-(R)-5-Hydroxy-3-methyl-pent-1-enyl)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-ol
881018-01-5

(2S,3R,5S,6R)-2-((E)-(R)-5-Hydroxy-3-methyl-pent-1-enyl)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-ol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9: 39 percent / aq. HCl / methanol / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(2S,3R,5S,6R)-2-((S)-5-Hydroxy-3-methyl-pentyl)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-ol

(2S,3R,5S,6R)-2-((S)-5-Hydroxy-3-methyl-pentyl)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-ol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9: 39 percent / aq. HCl / methanol / 20 °C
10: H2 / PtO2 / methanol / 50 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(S)-5-((2S,3R,5S,6R)-3-Hydroxy-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl)-3-methyl-pentanoic acid
881018-05-9

(S)-5-((2S,3R,5S,6R)-3-Hydroxy-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl)-3-methyl-pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: BH3*Me2S / tetrahydrofuran / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 °C
3.1: LiAlH4 / tetrahydrofuran / 0 °C
4.1: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5.1: TBAF / tetrahydrofuran / 20 °C
6.1: DEAD; PPh3 / tetrahydrofuran / 20 °C
7.1: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8.1: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9.1: 39 percent / aq. HCl / methanol / 20 °C
10.1: H2 / PtO2 / methanol / 50 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: CSA / methanol / 20 °C
13.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
13.2: Et3N / -78 - 20 °C
14.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C
15.1: TBAF / tetrahydrofuran / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentanal

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentanal

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: BH3*Me2S / tetrahydrofuran / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 °C
3.1: LiAlH4 / tetrahydrofuran / 0 °C
4.1: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5.1: TBAF / tetrahydrofuran / 20 °C
6.1: DEAD; PPh3 / tetrahydrofuran / 20 °C
7.1: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8.1: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9.1: 39 percent / aq. HCl / methanol / 20 °C
10.1: H2 / PtO2 / methanol / 50 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: CSA / methanol / 20 °C
13.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
13.2: Et3N / -78 - 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentan-1-ol
881018-03-7

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9: 39 percent / aq. HCl / methanol / 20 °C
10: H2 / PtO2 / methanol / 50 °C
11: imidazole / dimethylformamide / 20 °C
12: CSA / methanol / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-Butyl-[(2S,3R,5S,6R)-5-methoxy-2-((E)-(R)-5-methoxymethoxy-3-methyl-pent-1-enyl)-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane
881017-98-7

tert-Butyl-[(2S,3R,5S,6R)-5-methoxy-2-((E)-(R)-5-methoxymethoxy-3-methyl-pent-1-enyl)-6-methoxymethyl-2-methyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentanoic acid

(S)-5-[(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-3-methyl-pentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: BH3*Me2S / tetrahydrofuran / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 °C
3.1: LiAlH4 / tetrahydrofuran / 0 °C
4.1: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5.1: TBAF / tetrahydrofuran / 20 °C
6.1: DEAD; PPh3 / tetrahydrofuran / 20 °C
7.1: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8.1: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9.1: 39 percent / aq. HCl / methanol / 20 °C
10.1: H2 / PtO2 / methanol / 50 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: CSA / methanol / 20 °C
13.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
13.2: Et3N / -78 - 20 °C
14.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentyl]-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran

(2S,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentyl]-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
4: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5: TBAF / tetrahydrofuran / 20 °C
6: DEAD; PPh3 / tetrahydrofuran / 20 °C
7: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9: 39 percent / aq. HCl / methanol / 20 °C
10: H2 / PtO2 / methanol / 50 °C
11: imidazole / dimethylformamide / 20 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

C22H29Cl3O7

C22H29Cl3O7

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: BH3*Me2S / tetrahydrofuran / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 °C
3.1: LiAlH4 / tetrahydrofuran / 0 °C
4.1: (i-Pr)2NEt; DMAP / CH2Cl2 / 20 °C
5.1: TBAF / tetrahydrofuran / 20 °C
6.1: DEAD; PPh3 / tetrahydrofuran / 20 °C
7.1: MCPBA; NaHCO3 / CH2Cl2 / 20 °C
8.1: 79 percent / LHMDS / tetrahydrofuran / -78 - 20 °C
9.1: 39 percent / aq. HCl / methanol / 20 °C
10.1: H2 / PtO2 / methanol / 50 °C
11.1: imidazole / dimethylformamide / 20 °C
12.1: CSA / methanol / 20 °C
13.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
13.2: Et3N / -78 - 20 °C
14.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 20 °C
15.1: TBAF / tetrahydrofuran / 20 °C
16.1: Et3N / tetrahydrofuran / 0 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(3R)-4-(tert-butyl(dimethyl)silyloxy)-3-methylbutan-1-ol
147915-55-7

(3R)-4-(tert-butyl(dimethyl)silyloxy)-3-methylbutan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
3: LiAlH4 / tetrahydrofuran / 0 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

tert-butyl (R)-4-tert-butyldimethylsilyloxy-3-methylbutanoate
306739-86-6

tert-butyl (R)-4-tert-butyldimethylsilyloxy-3-methylbutanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BH3*Me2S / tetrahydrofuran / 20 °C
2: 2,6-lutidine / CH2Cl2 / 0 °C
View Scheme
(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid
185836-75-3

(R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid

(S)-2-methylpent-4-en-1-yl 4-methylbenzenesulfonate
132857-79-5

(S)-2-methylpent-4-en-1-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 85 percent / BH3*THF / tetrahydrofuran / 20 °C
2.1: pyridine / CH2Cl2 / 0 °C
3.1: DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C
4.1: NaHMDS / 1,2-dimethoxy-ethane; toluene / 20 °C
4.2: 1,2-dimethoxy-ethane; toluene / 20 °C
View Scheme

Butanedioic acid,2-methyl-, 4-(1,1-dimethylethyl) ester, (2R)- Specification

The Butanedioic acid,2-methyl-, 4-(1,1-dimethylethyl) ester, (2R)-, with the CAS registry number 185836-75-3, is also known as (R)-2-Methylsuccinic acid 4-tert-butyl ester. This chemical's molecular formula is C9H16O4 and molecular weight is 188.2209. Its systematic name is called (2R)-4-tert-butoxy-2-methyl-4-oxobutanoic acid.

Physical properties of Butanedioic acid,2-methyl-, 4-(1,1-dimethylethyl) ester, (2R)-: (1)ACD/LogP: 2.07; (2)ACD/LogD (pH 7.4): -1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 12; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.448; (11)Molar Refractivity: 47.008 cm3; (12)Molar Volume: 175.629 cm3; (13)Surface Tension: 35.673 dyne/cm; (14)Density: 1.072 g/cm3; (15)Flash Point: 104.694 °C; (16)Enthalpy of Vaporization: 57.305 kJ/mol; (17)Boiling Point: 281.928 °C at 760 mmHg; (18)Vapour Pressure: 0.001 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)C[C@H](C(=O)O)C
(2)InChI: InChI=1/C9H16O4/c1-6(8(11)12)5-7(10)13-9(2,3)4/h6H,5H2,1-4H3,(H,11,12)/t6-/m1/s1
(3)InChIKey: RSLMNCHJSYDERN-ZCFIWIBFBC

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