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155396-69-3

Basic Information
CAS No.: 155396-69-3
Name: (2R,4S,5R)-3-(tert-butoxycarbonyl)-2-(4-Methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid
Article Data: 3
Molecular Structure:
Molecular Structure of 155396-69-3 ((2R,4S,5R)-3-(tert-butoxycarbonyl)-2-(4-Methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid)
Formula: C22H25NO6
Molecular Weight: 399.444
Synonyms: (2R,4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid;(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid;(2R,4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid;
EINECS: 605-008-3
Density: 1.238g/cm3
Boiling Point: 573.799°C at 760 mmHg
Flash Point: 300.823°C
PSA: 85.30000
LogP: 4.09350
Synthetic route
155396-68-2

(2R,4S,5R)-5-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-2-(4-methoxy-phenyl)-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h;100%
153652-73-4

(2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
With KOH (or LiOH*H2O) In methanol; water Yield given;
4248-19-5

tert-butyl carbamate

ammonium salt of/the/ tert-butylsulfuric acid

ammonium salt of/the/ tert-butylsulfuric acid

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 68 percent / HCOOH / methanol; H2O / 21 h / 20 °C
2: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating
3: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
4: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
5: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
100-52-7

benzaldehyde

sodium cyanate

sodium cyanate

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 68 percent / HCOOH / methanol; H2O / 21 h / 20 °C
2: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating
3: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
4: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
5: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
150884-50-7

benzaldehyde N-boc imine

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
2: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
3: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
155396-71-7

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / K2CO3 / tetrahydrofuran / 12 h / Heating
2: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
3: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
4: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
155396-67-1

[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-carbamic acid tert-butyl ester

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
2: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme

2-(4'-methoxybenzyloxy)acetyl chloride

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / NaH / toluene / 1.) 20 deg C, 30 min, 2.) 20 deg C, 3 h
2: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
3: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
4: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
155396-70-6

N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LiN(Si(CH3)3)2 / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 15 min
2: 90 percent / DDQ, 4 Angstroem molecular sieves / CH2Cl2 / 14 h / 20 °C
3: 100 percent / LiOH, H2O2 / tetrahydrofuran; H2O / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h
View Scheme
2186-92-7

p-Anisaldehyde dimethyl acetal

155396-69-3

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74 percent / PPTS / toluene / 0.5 h / Heating
2: KOH (or LiOH*H2O) / methanol; H2O
View Scheme
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