Product Name

  • Name

    TERT-BUTYL (R)-(+)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATE

  • EINECS
  • CAS No. 95715-87-0
  • Article Data44
  • CAS DataBase
  • Density 1.129 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H19NO4
  • Boiling Point 302.738 °C at 760 mmHg
  • Molecular Weight 229.276
  • Flash Point 136.891 °C
  • Transport Information
  • Appearance Clear pale yellow oil
  • Safety 37/39-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 95715-87-0 (TERT-BUTYL (R)-(+)-4-FORMYL-2,2-DIMETHYL-3-OXAZOLIDINECARBOXYLATE)
  • Hazard Symbols IrritantXi
  • Synonyms 3-Oxazolidinecarboxylicacid, 4-formyl-2,2-dimethyl-, 1,1-dimethylethyl ester, (R)-;(4R)-4-Formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid tert-butyl ester;(R)-3-tert-Butoxycarbonyl-2,2-dimethyl-4-formyloxazolidine;(R)-4-Formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester;(R)-Garner aldehyde;1,1-Dimethylethyl(R)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate;ent-Garner's aldehyde;tert-Butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;tert-Butyl(R)-(+)-4-formyl-2,2-dimethyloxazolidine-3-carboxylate;tert-Butyl(R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylate;
  • PSA 55.84000
  • LogP 1.49520

Synthetic route

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
108149-63-9, 108149-65-1

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Stage #1: tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate With oxalyl dichloride In dichloromethane; dimethyl sulfoxide at -60 - -45℃; for 0.666667h; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at -45℃; Inert atmosphere;		100%
With Dess-Martin periodane In dichloromethane for 2h; Ambient temperature;93%
With Dess-Martin periodane; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 4h; Dess-Martin oxidation;90%
(R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine
167102-62-7

(R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h;100%
With lithium aluminium tetrahydride In 2-methyltetrahydrofuran at 0℃;100%
With lithium aluminium tetrahydride In tetrahydrofuran for 2.33333h; Inert atmosphere; Cooling;92%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 30℃; for 3h;100 g
methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate
108149-60-6, 95715-86-9

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -60 - 0℃; for 2.5h;95%
With diisobutylaluminium hydride In toluene at -78 - -70℃; for 4h; Inert atmosphere;89%
With diisobutylaluminium hydride In toluene at -78℃; for 2h;85%
(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid
660852-86-8

(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 0℃; for 2h; Swern Oxidation;85%
2,2-dimethyl-oxazole-3-carboxylic acid tert-butyl ester

2,2-dimethyl-oxazole-3-carboxylic acid tert-butyl ester

dicarbonylacetylacetonato rhodium (I)

dicarbonylacetylacetonato rhodium (I)

A

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

B

tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate
95715-87-0, 102308-32-7, 144070-30-4, 127589-93-9

tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
With 2,2',2'',2'''-(1,2-phenylenebis((1R,3R)-tetrahydro-5,8-dioxo-1H-(1,2,4)diazaphospholo(1,2-a)pyridazine-2,1,3(3H)-triyl))tetrakis(N-(1S)-1-phenylethyl)-benzamide In tetrahydrofuran at 55℃; under 7240.26 Torr; for 72h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;A 71%
B n/a
...Expand
(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester
95715-86-9, 108149-60-6

(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -80℃; for 4h; Automated synthesizer;71%
D-Serine
312-84-5

D-Serine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multistep reaction;51%
...Expand
methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate
108149-60-6, 95715-86-9

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

A

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

B

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
108149-63-9, 108149-65-1

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -78℃;A 40%
B 8%
1,1-dimethylethyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

1,1-dimethylethyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

A

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
102308-32-7

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

B

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C to r.t.; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
(R)-4-(1,2-Dihydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-4-(1,2-Dihydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
With sodium periodate; silica gel In dichloromethane Ambient temperature; Yield given;
D-Serine
312-84-5

D-Serine

(CH3)2CX, (CH3)3CHOCOX

(CH3)2CX, (CH3)3CHOCOX

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Yield given. Multistep reaction;
(R)-N-tert-butoxycarbonyl serine
3262-72-4, 3850-40-6, 6368-20-3, 90582-28-8, 84311-18-2

(R)-N-tert-butoxycarbonyl serine

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / K2CO3 / dimethylformamide / 1.5 h / 0 - 20 °C
2: 80 percent / p-TsOH / benzene / 1 h / Heating
3: 75 percent / DIBAL-H / toluene / 2 h / -78 °C
View Scheme
Multi-step reaction with 3 steps
1: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, N-methylmorpholine / CH2Cl2 / 1 h / -15 °C
2: BF3*Et2O / acetone / 1.5 h / Ambient temperature
3: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 0.5 h / 0 °C
2: 80 percent / TsOH*H2O / benzene / 0.5 h
3: 85 percent / diisobutylaluminum hydride (DIBAL) / toluene / 2 h / -78 °C
View Scheme
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
95715-85-8

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / p-TsOH / benzene / 1 h / Heating
2: 75 percent / DIBAL-H / toluene / 2 h / -78 °C
View Scheme
Multi-step reaction with 3 steps
1: 75 percent / TsOH*H2O / benzene / Heating
2: 96 percent / NaBH4, LiCl / ethanol; tetrahydrofuran / 4 h / Ambient temperature
3: 1.) trifluoroacetic anhydride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, from -78 deg C to 25 deg C
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / TsOH*H2O / benzene / 0.5 h
2: 85 percent / diisobutylaluminum hydride (DIBAL) / toluene / 2 h / -78 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaOH / dioxane; H2O / 48 h / 0 - 20 °C
2: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, N-methylmorpholine / CH2Cl2 / 1 h / -15 °C
3: BF3*Et2O / acetone / 1.5 h / Ambient temperature
4: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 100 percent / Et3N / tetrahydrofuran / a) RT, 6 h, b) 50 deg C, 2 h
2: 98 percent / LiBH4 / tetrahydrofuran / 12 h / Ambient temperature
3: 98 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
4: 95 percent / H2 / Pd/C / ethyl acetate / 24 h / Ambient temperature
5: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 1 N NaOH / dioxane / 1.) 5 deg C, 30 min, 2.) RT, 3.5 h
2: 0.5 h / 0 °C
3: 80 percent / TsOH*H2O / benzene / 0.5 h
4: 85 percent / diisobutylaluminum hydride (DIBAL) / toluene / 2 h / -78 °C
View Scheme
tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate
167102-61-6

tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BF3*Et2O / acetone / 1.5 h / Ambient temperature
2: 100 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / 2 h / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 2.33 h / Inert atmosphere; Cooling
View Scheme
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / acetone / 0.05 h / 25 - 30 °C
2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 3 h / 0 - 30 °C
View Scheme
N-(tert-butoxycarbonyl)-L-serine methyl ester
2766-43-0

N-(tert-butoxycarbonyl)-L-serine methyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: imidazole / CH2Cl2 / 12 h / Ambient temperature
2: LiBH4 / tetrahydrofuran / 12 h / Ambient temperature
3: 94 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
4: 98 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
5: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 93 percent / BF3OEt2 / acetone / 12 h / Ambient temperature
2: 78 percent / DIBAL-H / toluene / 1.5 h / -78 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1H-imidazole / dichloromethane / 0 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux; Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C
5.2: 0.08 h / -78 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 25 °C / Automated synthesizer
2: diisobutylaluminium hydride / toluene / 4 h / -80 °C / Automated synthesizer
View Scheme
(S)-tert-butyl (1-hydroxy-4-(methylthio)butan-2-yl)carbamate
51372-93-1

(S)-tert-butyl (1-hydroxy-4-(methylthio)butan-2-yl)carbamate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / BF3*Et2O / acetone / Ambient temperature
2: 93 percent / NaIO4, NaHCO3 / methanol; H2O / 0 °C
3: 69 percent / various solvent(s) / 6 h / 175 - 180 °C
4: OsO4, NMO / acetone / Ambient temperature
5: NaIO4, SiO2 / CH2Cl2 / Ambient temperature
View Scheme
N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol
79069-15-1

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
2: 95 percent / H2 / Pd/C / ethyl acetate / 24 h / Ambient temperature
3: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate
80963-10-6

methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / LiBH4 / tetrahydrofuran / 12 h / Ambient temperature
2: 98 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
3: 95 percent / H2 / Pd/C / ethyl acetate / 24 h / Ambient temperature
4: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate
133625-87-3

tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: OsO4, NMO / acetone / Ambient temperature
2: NaIO4, SiO2 / CH2Cl2 / Ambient temperature
View Scheme
methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate
159846-14-7

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(tert-butoxy)carbonylamino]propanoate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiBH4 / tetrahydrofuran / 12 h / Ambient temperature
2: 94 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
3: 98 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
4: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
(S)-4-Benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
198417-68-4

(S)-4-Benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / H2 / Pd/C / ethyl acetate / 24 h / Ambient temperature
2: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate
198417-69-5

tert-butyl [(1R)-2-(tert-butyldiphenylsilyloxy)-1-(hydroxymethyl)-ethyl]carbamate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / BF3*Et2O / acetone / 2 h / Ambient temperature
2: 98 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
3: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
198417-70-8

(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
2: 93 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
View Scheme
(S)-2,2-Dimethyl-4-(2-methylsulfanyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester
197218-81-8

(S)-2,2-Dimethyl-4-(2-methylsulfanyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 93 percent / NaIO4, NaHCO3 / methanol; H2O / 0 °C
2: 69 percent / various solvent(s) / 6 h / 175 - 180 °C
3: OsO4, NMO / acetone / Ambient temperature
4: NaIO4, SiO2 / CH2Cl2 / Ambient temperature
View Scheme
(S)-4-(2-Methanesulfinyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
197218-82-9

(S)-4-(2-Methanesulfinyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / various solvent(s) / 6 h / 175 - 180 °C
2: OsO4, NMO / acetone / Ambient temperature
3: NaIO4, SiO2 / CH2Cl2 / Ambient temperature
View Scheme
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / dioxane; H2O
2: methanol
3: CSA / acetone
4: LiAlH4 / diethyl ether / 0 °C
5: -78 °C / Swern ox.
View Scheme
(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate
126645-26-9

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux; Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C
4.2: 0.08 h / -78 - 0 °C
View Scheme
(R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester
152491-85-5

(R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux; Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C
3.2: 0.08 h / -78 - 0 °C
View Scheme
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
108149-63-9, 108149-65-1

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Conditions
ConditionsYield
With zirconium(IV) tetraisopropoxide 2-propanol; 1,1'-bi-2-naphthol In toluene at 20℃; for 4h;100%
With sodium tetrahydroborate In methanol at 0℃; for 1h;84%
With zirconium(IV) tetraisopropoxide 2-propanol; 4 Angstroem MS; 1,1'-bi-2-naphthol In isopropyl alcohol; toluene at 20℃; for 12h;70%
With sodium tetrahydroborate In tetrahydrofuran; isopropyl alcohol for 0.5h;64%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

allylmagnesium bromide
1730-25-2

allylmagnesium bromide

1,1-dimethylethyl (4R)-(1'-hydroxy-3'-butenyl)-2,2-dimethyl-3-oxazolidinecarboxylate
220317-60-2

1,1-dimethylethyl (4R)-(1'-hydroxy-3'-butenyl)-2,2-dimethyl-3-oxazolidinecarboxylate

Conditions
ConditionsYield
100%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

ethyl 2-methyl-3-[3-(tert-butoxycarbonyl)-2,2-dimethyl-(4S)-oxazolidinyl]prop-(2E)-enoate
916912-39-5

ethyl 2-methyl-3-[3-(tert-butoxycarbonyl)-2,2-dimethyl-(4S)-oxazolidinyl]prop-(2E)-enoate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h;100%
In benzene Wittig reaction; Reflux;84%
In dichloromethane at 20℃;
O-methylresorcine
150-19-6

O-methylresorcine

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
925703-63-5

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: O-methylresorcine With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;		100%
C27H31N5O6S*2ClH

C27H31N5O6S*2ClH

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

C38H50N6O9S
1111235-29-0

C38H50N6O9S

Conditions
ConditionsYield
Stage #1: C27H31N5O6S*2ClH; (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine With sodium tris(acetoxy)borohydride; triethylamine In dichloromethane at 20℃; for 16h;
Stage #2: With water; potassium carbonate In dichloromethane at 20℃;		100%
1-ethynyl-4-(n-pentyl)benzene
79887-10-8

1-ethynyl-4-(n-pentyl)benzene

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

C24H35NO4
1207432-32-3

C24H35NO4

Conditions
ConditionsYield
Stage #1: 1-ethynyl-4-(n-pentyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere;
Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #3: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at -78 - -60℃; for 5h; Inert atmosphere;		100%
Sesamol
533-31-3

Sesamol

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (R)-4-((R)-hydroxy(6-hydroxybenzo[d][1,3]dioxol-5-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
925703-84-0

tert-butyl (R)-4-((R)-hydroxy(6-hydroxybenzo[d][1,3]dioxol-5-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: Sesamol With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;		99%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(2E',4S)-4-(2'-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
134525-18-1, 131713-27-4, 144070-31-5, 149406-02-0

(2E',4S)-4-(2'-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane In toluene at 110℃; for 12h; Wittig type reaction; Inert atmosphere; stereoselective reaction;99%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

4-methylbenzo[1,3]dioxol-5-ol
187040-03-5

4-methylbenzo[1,3]dioxol-5-ol

(R)-4-[(R)-Hydroxy-(6-hydroxy-7-methyl-benzo[1,3]dioxol-5-yl)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
654643-98-8

(R)-4-[(R)-Hydroxy-(6-hydroxy-7-methyl-benzo[1,3]dioxol-5-yl)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With methylmagnesium chloride In tetrahydrofuran; dichloromethane at 20℃;98%
Stage #1: 4-methylbenzo[1,3]dioxol-5-ol With methylmagnesium chloride In tetrahydrofuran
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane Further stages.;		98%
Stage #1: 4-methylbenzo[1,3]dioxol-5-ol With methylmagnesium chloride In tetrahydrofuran; hexane at 20℃; for 0.5h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane; dichloromethane at 20℃;		98%
3-bromo-3,3-difluropropene
420-90-6

3-bromo-3,3-difluropropene

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

C14H23F2NO4
1056467-63-0

C14H23F2NO4

Conditions
ConditionsYield
With indium; lithium iodide In N,N-dimethyl-formamide98%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(cyclopropylmethyl)triphenylphosphonium bromide
14799-82-7

(cyclopropylmethyl)triphenylphosphonium bromide

(S)-tert-butyl 4-(2-cyclopropylvinyl)-2,2-dimethyloxazolidine-3-carboxylate
1222186-28-8

(S)-tert-butyl 4-(2-cyclopropylvinyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: (cyclopropylmethyl)triphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at -78 - 20℃; for 1h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran at -78℃;		96%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

(4S)-1,1-Dimethylethyl 4-<(E)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate
129483-65-4

(4S)-1,1-Dimethylethyl 4-<(E)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate

Conditions
ConditionsYield
In benzene Ambient temperature;95%
In toluene at 0 - 20℃; for 40h;77%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

ethylamine
75-04-7

ethylamine

(S)-4-ethylaminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
1048351-33-2

(S)-4-ethylaminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine; ethylamine In methanol at 20℃; for 1.5h; Molecular sieve;
Stage #2: With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr;		95%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4S)-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S)-4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In acetonitrile at 25℃;95%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

N-ε-(2-Chloro-CBZ)-L-lysine allyl ester hydrochloride
144156-17-2

N-ε-(2-Chloro-CBZ)-L-lysine allyl ester hydrochloride

(S)-4-{[(S)-1-Allyloxycarbonyl-5-(2-chloro-benzyloxycarbonylamino)-pentylamino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
144156-07-0

(S)-4-{[(S)-1-Allyloxycarbonyl-5-(2-chloro-benzyloxycarbonylamino)-pentylamino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol for 1h; Ambient temperature;94%
3-bromofurane
22037-28-1

3-bromofurane

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

C15H23NO5
1105713-64-1

C15H23NO5

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;93%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

sodium chlorodifluoroacetate
1895-39-2

sodium chlorodifluoroacetate

C12H19F2NO3

C12H19F2NO3

Conditions
ConditionsYield
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;92.31%
carbon tetrabromide
558-13-4

carbon tetrabromide

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(S)-tert-butyl 4-(2,2-dibromovinyl)-2,2-dimethyloxazolidine-3-carboxylate
130418-98-3

(S)-tert-butyl 4-(2,2-dibromovinyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0 - 20℃; for 2.33333h;92%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at -30℃; for 0.666667h; Inert atmosphere;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine With triethylamine In dichloromethane at -60 - 0℃; for 2.5h; Inert atmosphere;
Stage #3: With sodium hydrogencarbonate In dichloromethane; water		88%
With triphenylphosphine72%
With triethylamine; triphenylphosphine 1.) CH2Cl2, -20 deg C, 30 min; 2.) CH2Cl2, -60 deg C, 30 min, r.t., overnight; Multistep reaction;
With triethylamine; triphenylphosphine 1) CH2Cl2, -20 deg C, 30 min; 2) CH2Cl2, -60 deg C, 30 min, rt, overnight; Yield given. Multistep reaction;
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4R)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
768387-35-5

(4R)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
at -78 - -20℃; for 1.5h;92%
Addition;81%
In tetrahydrofuran -78 deg C -> -50 deg C, 2 h;74%
2,2,4,4-Tetrakis(trifluoromethyl)-1,3-dithietane
791-50-4

2,2,4,4-Tetrakis(trifluoromethyl)-1,3-dithietane

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

2,2-dimethyl-4-(3,3,3-trifluoro-2-trifluoromethyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester
340714-52-5

2,2-dimethyl-4-(3,3,3-trifluoro-2-trifluoromethyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine In diethyl ether at -78 - 20℃; for 72h; Wittig reaction;92%
With triphenylphosphine In diethyl ether at -78 - 20℃; for 72h;92%
tetravinyltin (IV)
1112-56-7

tetravinyltin (IV)

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

A

(1'R,4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-propen-1-yl)-1,3-oxazolidine
114301-35-8

(1'R,4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-hydroxy-2-propen-1-yl)-1,3-oxazolidine

B

(4R,1'S)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
114301-34-7

(4R,1'S)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: tetravinyltin (IV) With methyllithium In diethyl ether at 0℃; for 0.25h; Inert atmosphere;
Stage #2: With zinc dibromide In diethyl ether at 20℃; for 1h; Inert atmosphere;
Stage #3: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In diethyl ether at -35 - 20℃; Inert atmosphere;		A 92%
B n/a
Stage #1: tetravinyltin (IV) With methyllithium; zinc dibromide In diethyl ether at 20℃; for 1h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In diethyl ether at 20℃; for 2h; Title compound not separated from byproducts;
Stage #1: tetravinyltin (IV) With methyllithium In diethyl ether at 0℃; for 0.25h;
Stage #2: With zinc dibromide In diethyl ether at 20℃; for 1h;
Stage #3: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine With zinc dibromide In diethyl ether at -78 - 20℃; Title compound not separated from byproducts;
...Expand
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(bromomethyl)pentafluorobenzene
1765-40-8

(bromomethyl)pentafluorobenzene

(S)-2,2-Dimethyl-4-((E)-2-pentafluorophenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester
752244-60-3

(S)-2,2-Dimethyl-4-((E)-2-pentafluorophenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (bromomethyl)pentafluorobenzene With triphenylphosphine In tetrahydrofuran for 0.25h;
Stage #2: With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.5h; Wittig olefination;
Stage #3: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran at -78 - 20℃; for 14h; Wittig olefination;		92%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4R)-(1-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
488727-69-1

(4R)-(1-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 20℃; for 3h;91%
In tetrahydrofuran at -78 - 25℃; Inert atmosphere;77%
tetravinyltin (IV)
1112-56-7

tetravinyltin (IV)

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(4R)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
768387-35-5

(4R)-4-(1-hydroxy-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium In diethyl ether at -78℃; for 2h;91%
3,4-dimethoxyphenol
2033-89-8

3,4-dimethoxyphenol

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
925703-87-3

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4,5-dimethoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: 3,4-dimethoxyphenol With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;		91%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

3-chloro-aniline
108-42-9

3-chloro-aniline

(S)-4-[(3-chlorophenylamino)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
1048351-01-4

(S)-4-[(3-chlorophenylamino)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride; zinc(II) chloride In methanol at 20 - 40℃; for 3h; Inert atmosphere;91%
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

(2E',4S)-4-(2'-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
134525-18-1, 131713-27-4, 144070-31-5, 149406-02-0

(2E',4S)-4-(2'-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2.5h; Heating;90%
In benzene at 20℃; for 36h;85%
In tetrahydrofuran at 25℃; for 12h; Condensation;72%

(R)-(+)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde Specification

The (R)-(+)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, with the CAS registry number 95715-87-0, is also known as (+)-N-Boc-N,O-isopropylidene-D-serinal. It belongs to the product category of Pharmacetical. This chemical's molecular formula is C11H19NO4 and molecular weight is 229.27. Its IUPAC name is called tert-butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate. This chemical is clear pale yellow oil.

Physical properties of (R)-(+)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.379; (4)ACD/LogD (pH 7.4): 1.379; (5)ACD/BCF (pH 5.5): 6.583; (6)ACD/BCF (pH 7.4): 6.583; (7)ACD/KOC (pH 5.5): 134.101; (8)ACD/KOC (pH 7.4): 134.101; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.5; (13)Molar Refractivity: 59.752 cm3; (14)Molar Volume: 202.994 cm3; (15)Surface Tension: 40.672 dyne/cm; (16)Density: 1.129 g/cm3; (17)Flash Point: 136.891 °C; (18)Enthalpy of Vaporization: 54.298 kJ/mol; (19)Boiling Point: 302.738 °C at 760 mmHg; (20)Vapour Pressure: 0.001 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1(N(C(CO1)C=O)C(=O)OC(C)(C)C)C
(2)Isomeric SMILES: CC1(N([C@H](CO1)C=O)C(=O)OC(C)(C)C)C
(3)InChI: InChI=1S/C11H19NO4/c1-10(2,3)16-9(14)12-8(6-13)7-15-11(12,4)5/h6,8H,7H2,1-5H3/t8-/m0/s1
(4)InChIKey: PNJXYVJNOCLJLJ-QMMMGPOBSA-N

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