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inquirymethyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h; | 90% |
methanol
(-)-(2R,3S)-sodium 3-(4-methoxyphenyl)glycidate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With triethylamine; 2-chloro-1-methylpyridinium sulfate In dichloromethane; 1,2-dichloro-ethane Ambient temperature; | 83% |
methanol
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane at -78℃; Inert atmosphere; | 79% |
3-(4-methoxy-phenyl)acrylic acid methyl ester
butan-1-ol
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-trans-(4-methoxyphenyl)glycidic acid butyl ester
C
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
Stage #1: 3-(4-methoxy-phenyl)acrylic acid methyl ester With Oxone; (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid cyclic ester In 1,4-dioxane; water for 26h; Stage #2: butan-1-ol With Serratia marcescens lipase on celit for 25h; Further stages.; | A 76% B 6.2% C 1.6% |
methyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propionate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With potassium carbonate In methanol; diethyl ether at 0 - 5℃; for 0.5h; Yields of byproduct given. Title compound not separated from byproducts; | A 74% B n/a |
methyl trans-3-(4-methoxyphenyl)glycidate
(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol
B
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
C
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With lipase type VII In cyclohexane at 33℃; for 9.5h; Enzymatic reaction; | A 45.6% B n/a C n/a |
With lipase type VII In diethyl ether; hexane at 26℃; for 13.5h; Enzymatic reaction; | A 23.1% B n/a C n/a |
methyl trans-3-(4-methoxyphenyl)glycidate
iso-butanol
B
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
C
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With lipase AMANO for 9h; Enzymatic reaction; | A 37.6% B n/a C n/a |
With lipase AMANO In cyclohexane at 40℃; for 12h; Enzymatic reaction; | A 30% B n/a C n/a |
2-(N,N-dimethylamino)ethanol
methyl trans-3-(4-methoxyphenyl)glycidate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With 5A molecular sieve; Novozym 435 (Candida antarctica lipase, EC 3.1.1.3) In toluene at 20℃; for 4h; Product distribution; Enzyme kinetics; Further Variations:; Solvents; Reagents; Reaction partners; Enzymatic reaction; | A 37.5% B n/a |
methyl trans-3-(4-methoxyphenyl)glycidate
A
4-Methoxyphenylacetaldehyde
B
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
C
(2S,3R)-trans-(4-methoxyphenyl)glycidic acid
Conditions | Yield |
---|---|
In cyclohexane; water for 1.5h; Ambient temperature; enzymatic hydrolysis by lipase from Candida cylindracea (CCL), pH 7.4, other enzymes; enzymatic transesterification; | A n/a B 35% C n/a |
In cyclohexane; water for 1.5h; Ambient temperature; enzymatic hydrolysis by lipase from Candida cylindracea (CCL), pH 7.4; | A n/a B 35% C n/a |
methyl 3-(4-methoxyphenyl)glycidate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-trans-(4-methoxyphenyl)glycidic acid
Conditions | Yield |
---|---|
With water In acetone at 25℃; Rhizopus arrhizus mycelium lipase, pH 7; |
methyl 3-(4-methoxyphenyl)glycidate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
3-(4-methoxyphenyl)acrylic acid methyl ester
A
(2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester
B
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
C
(2S,3R)-methyl p-methoxycinnamate epoxide
D
methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With sodium hypochlorite; 4-Phenylpyridine 1-oxide; (salen)Mn(III)-complex In water; 1,2-dichloro-ethane at 4℃; for 12h; Yield given. Yields of byproduct given; |
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With sodium methylate In methanol at 0 - 20℃; for 1.66667h; Yield given. Title compound not separated from byproducts; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 4h; Title compound not separated from byproducts; |
methanol
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at -20 - 0℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(S)-2-Chloro-3-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With sodium methylate In methanol at 0 - 20℃; | |
With sodium methylate In methanol at 0 - 20℃; for 0.75h; | 894 mg |
1-pyrrolidineethanol
methyl trans-3-(4-methoxyphenyl)glycidate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With 5A molecular sieve; Novozym 435 (Candida antarctica lipase, EC 3.1.1.3) In toluene at 20℃; Enzymatic reaction; Title compound not separated from byproducts.; |
1-piperidinoethanol
methyl trans-3-(4-methoxyphenyl)glycidate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With 5A molecular sieve; Novozym 435 (Candida antarctica lipase, EC 3.1.1.3) In toluene at 20℃; Enzymatic reaction; Title compound not separated from byproducts.; |
3-Dimethylamino-1-propanol
methyl trans-3-(4-methoxyphenyl)glycidate
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With 5A molecular sieve; Novozym 435 (Candida antarctica lipase, EC 3.1.1.3) In toluene at 20℃; Enzymatic reaction; Title compound not separated from byproducts.; |
methyl trans-3-(4-methoxyphenyl)glycidate
2-(Diethylamino)ethanol
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With 5A molecular sieve; Novozym 435 (Candida antarctica lipase, EC 3.1.1.3) In toluene at 20℃; Enzymatic reaction; Title compound not separated from byproducts.; |
3-(4-methoxy-phenyl)acrylic acid methyl ester
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
With Oxone; sodium hydrogencarbonate; chiral binaphthyl ketone C25H16O5 In 1,4-dioxane; water at 5 - 27℃; for 27h; Product distribution; Further Variations:; Catalysts; Solvents; | |
With Oxone; (R)dinaphtho[2,1-g:1,2-i][1,5]dioxacycloundecin-3,6,9-trione; sodium hydrogencarbonate In 1,4-dioxane; water at 5 - 27℃; for 50h; | |
With Oxone; (2S,5R)-2-fluoro-2-methyl5-(2-methyl-oxiranyl)cyclohexanone In 1,4-dioxane; water at 20℃; for 8h; Title compound not separated from byproducts; |
methanol
A
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
B
(2S,3R)-methyl p-methoxycinnamate epoxide
Conditions | Yield |
---|---|
Stage #1: 1-[(2E)-3-(4-methoxyphenyl)-1-oxo-2-propenyl]-4-phenyl-1H-imidazole With tert.-butylhydroperoxide; La-(S)-BINOL-Ph3AsO; 4 A molecular sieve In tetrahydrofuran; toluene at 20℃; for 5h; Stage #2: methanol In tetrahydrofuran; toluene at 20℃; Title compound not separated from byproducts; | |
Stage #1: 1-[(2E)-3-(4-methoxyphenyl)-1-oxo-2-propenyl]-4-phenyl-1H-imidazole With tert.-butylhydroperoxide; lanthanum(III) isopropoxide; 4 A molecular sieve; triphenylarsineoxide; (S)-[1,1']-binaphthalenyl-2,2'-diol In tetrahydrofuran; decane at 20℃; for 6h; Stage #2: methanol In tetrahydrofuran; toluene Further stages. Title compound not separated from byproducts.; |
methyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propionate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 5 - 20℃; for 0.583333h; |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 5 - 20℃; for 0.583333h; |
3-(4-methoxy-phenyl)acrylic acid methyl ester
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 66 percent / KBrO3; aq. H2SO4; aq. NaHSO3 / acetonitrile / 36 h 2.1: 94 percent / DMAP / CH2Cl2 / 20 °C 3.1: lipase AS Amano; aq. phosphate buffer / toluene / 48 h / 30 °C / pH 7.0 3.2: lipase AS Amano; aq. phosphate buffer / toluene / 33 h / 30 °C / pH 7.0 4.1: HCl / methanol / 24 h / 20 °C 5.1: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: 65 percent / HIO4*2H2O; aq. NaHSO3 / acetonitrile / 48 h / 25 °C 2: 90 percent / DMAP / CH2Cl2 / 20 °C 3: lipase AS Amano; aq. phosphate buffer / toluene / 45 h / 30 °C / pH 7.0 4: HCl / methanol / 24 h / 20 °C 5: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 94 percent / DMAP / CH2Cl2 / 20 °C 2.1: lipase AS Amano; aq. phosphate buffer / toluene / 48 h / 30 °C / pH 7.0 2.2: lipase AS Amano; aq. phosphate buffer / toluene / 33 h / 30 °C / pH 7.0 3.1: HCl / methanol / 24 h / 20 °C 4.1: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / DMAP / CH2Cl2 / 20 °C 2: lipase AS Amano; aq. phosphate buffer / toluene / 45 h / 30 °C / pH 7.0 3: HCl / methanol / 24 h / 20 °C 4: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
(2S,3S)-methyl 3-acetoxy-2-bromo-3-(4-methoxyphenyl)-propanoate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl / methanol / 24 h / 20 °C 2: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lipase AS Amano; aq. phosphate buffer / toluene / 48 h / 30 °C / pH 7.0 1.2: lipase AS Amano; aq. phosphate buffer / toluene / 33 h / 30 °C / pH 7.0 2.1: HCl / methanol / 24 h / 20 °C 3.1: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
(2S,3S)-methyl 3-acetoxy-2-iodo-3-(4-methoxyphenyl)-propanoate
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl / methanol / 24 h / 20 °C 2: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lipase AS Amano; aq. phosphate buffer / toluene / 45 h / 30 °C / pH 7.0 2: HCl / methanol / 24 h / 20 °C 3: DBU / CH2Cl2 / 0.58 h / 5 - 20 °C View Scheme |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
2-amino-benzenethiol
(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 6h; Reflux; optical yield given as %ee; | 90% |
With triethylamine In trichloroacetic acid |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
2-mercapto-3-nitrothiophene
(-)-(2S,3S)-methyl-2-hydroxy-3-(4-methoxyphenyl)-3-(3-nitro-2-thienylthio)propionate
Conditions | Yield |
---|---|
In chlorobenzene at 130℃; for 2h; | 42% |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
2-amino-benzenethiol
(+)-(2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propanoic acid methyl ester
Conditions | Yield |
---|---|
With iron(III) chloride In chlorobenzene at 115℃; for 0.75h; | |
In toluene | |
In 5,5-dimethyl-1,3-cyclohexadiene |
methyl (2R,3S)-3-(4-methoxyphenyl)glycidate
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 3h; Ambient temperature; |
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