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20989-17-7 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 20989-17-7 differently. You can refer to the following data:
1. (S)-(+)-2-Phenylglycinol is a chiral arylalkylamine used as organocatalysts. Used in the synthesis and chiral recognition properties of novel fluorescent chemosensors for amino acid.
2. (S)-(+)-2-Phenylglycinol is used in the synthesis of chiral, unsymmetrical bisoxazolines. It is used as a reagent for the resolution of acids via the easily hydrolyzed amides.

Check Digit Verification of cas no

The CAS Registry Mumber 20989-17-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,9,8 and 9 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 20989-17:
(7*2)+(6*0)+(5*9)+(4*8)+(3*9)+(2*1)+(1*7)=127
127 % 10 = 7
So 20989-17-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1

20989-17-7 Well-known Company Product Price

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  • Detail
  • TCI America

  • (P1294)  (S)-(+)-2-Phenylglycinol  >97.0%(GC)(T)

  • 20989-17-7

  • 5g

  • 890.00CNY

  • Detail
  • TCI America

  • (P1294)  (S)-(+)-2-Phenylglycinol  >97.0%(GC)(T)

  • 20989-17-7

  • 25g

  • 2,990.00CNY

  • Detail
  • Alfa Aesar

  • (L13265)  (S)-(+)-2-Phenylglycinol, 98+%   

  • 20989-17-7

  • 1g

  • 417.0CNY

  • Detail
  • Alfa Aesar

  • (L13265)  (S)-(+)-2-Phenylglycinol, 98+%   

  • 20989-17-7

  • 5g

  • 1330.0CNY

  • Detail
  • Alfa Aesar

  • (L13265)  (S)-(+)-2-Phenylglycinol, 98+%   

  • 20989-17-7

  • 25g

  • 5109.0CNY

  • Detail
  • Aldrich

  • (282693)  (S)-(+)-2-Phenylglycinol  98%

  • 20989-17-7

  • 282693-1G

  • 285.48CNY

  • Detail
  • Aldrich

  • (282693)  (S)-(+)-2-Phenylglycinol  98%

  • 20989-17-7

  • 282693-5G

  • 972.27CNY

  • Detail

20989-17-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(+)-2-Phenylglycinol

1.2 Other means of identification

Product number -
Other names H-PHG-OL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20989-17-7 SDS

20989-17-7Synthetic route

N-<(2R,4E)-2-Methyl-4-hexenoyl>-S-phenylglycinol
118958-06-8

N-<(2R,4E)-2-Methyl-4-hexenoyl>-S-phenylglycinol

A

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

B

(2R,4E)-2-Methyl-4-hexenoic acid
93553-73-2

(2R,4E)-2-Methyl-4-hexenoic acid

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 70 - 80℃; for 3h;A 92%
B 99%
(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;97%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;97%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;95%
tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate
117049-14-6

tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
In acetonitrile at 300℃; under 75007.5 Torr;93%
(S)-Phenylglycine methyl ester
6591-61-3, 24461-61-8, 26682-99-5, 37760-98-8

(S)-Phenylglycine methyl ester

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Reflux;88%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.5h; Reflux;88%
Stage #1: (S)-Phenylglycine methyl ester With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 0.25h;
Stage #2: With methanol In tetrahydrofuran at 65℃; stereospecific reaction;
73%
With sodium tetrahydroborate In methanol at 20℃; for 1h;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Cooling with ice; Inert atmosphere;
(S)-4-phenyl-2-oxazolidinone
99395-88-7

(S)-4-phenyl-2-oxazolidinone

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With 3-azapentane-1,5-diamine at 140℃; for 18h;85%
L-2-phenylglycine methyl ester hydrochloride
15028-39-4

L-2-phenylglycine methyl ester hydrochloride

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol 1) RT, 9h, b) 5.5h, reflux, c) RT, 8h;83%
With sodium tetrahydroborate In ethanol; water for 5.5h; Heating;
Stage #1: L-2-phenylglycine methyl ester hydrochloride With triethylamine In methanol; diethyl ether at -10℃; for 1h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;
4.4 g
N-(2-methoxymethoxy-1-phenyl-ethyl)-acetamide
217650-36-7

N-(2-methoxymethoxy-1-phenyl-ethyl)-acetamide

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
In methanol Hydrolysis; Acid hydrolysis;81%
benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate
130406-31-4

benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol for 0.25h;80%

A

(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

B

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogenchloride; (S)-(+)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In dichloromethane; water at 21.84℃; pH=2.32; Centrifugal contactor separators; Resolution of racemate; optical yield given as %ee;A n/a
B 36%
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up;
With 3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In tetrachloromethane at 6℃; pH=3; aq. buffer; enantioselective reaction;
(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

A

(2S)-(-)-2-amino-2-phenylethanol N-borane

(2S)-(-)-2-amino-2-phenylethanol N-borane

B

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Stage #1: (S)-2-phenylglycine With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran; diethyl ether at 0 - 20℃; for 20h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 2h;
A 27%
B 33%
(S)-phenylglycine ethyl ester
15962-49-9

(S)-phenylglycine ethyl ester

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
(S)-2-azido-2-phenylethanol
126923-25-9

(S)-2-azido-2-phenylethanol

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating; Yield given;
(1S,2S,5S)-3-[(E)-(S)-2-Hydroxy-1-phenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol
127718-96-1

(1S,2S,5S)-3-[(E)-(S)-2-Hydroxy-1-phenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydroxylamine acetate In ethanol for 20h; Ambient temperature; Yield given;
tert-butyl 2-hydroxy-1-phenylethylcarbamate
102089-74-7, 117049-14-6, 138457-46-2, 67341-01-9

tert-butyl 2-hydroxy-1-phenylethylcarbamate

A

(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

B

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine
126927-38-6

(1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogen S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415.;
(R)-Styrene oxide
20780-53-4

(R)-Styrene oxide

A

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

B

(R)-2-Amino-1-phenylethanol
2549-14-6

(R)-2-Amino-1-phenylethanol

Conditions
ConditionsYield
With ammonium hydroxide In water at 130℃; under 9000.72 Torr; microwave irradiation;A 20 % Chromat.
B 80 % Chromat.
(S)-2-Hydrazino-2-phenyl-ethanol

(S)-2-Hydrazino-2-phenyl-ethanol

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogen; nickel In methanol at 25℃; under 25857.4 Torr; for 28h;0.136 g
C18H26N2O5
1026035-75-5

C18H26N2O5

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4 / methanol
2: TFA / CH2Cl2 / 3 h / 20 °C
3: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr
View Scheme
C18H28N2O5
1027539-12-3

C18H28N2O5

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TFA / CH2Cl2 / 3 h / 20 °C
2: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr
View Scheme
phenylacetaldehyde
122-78-1

phenylacetaldehyde

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: D-proline / CH2Cl2 / 3 h / 20 °C
2: NaBH4 / methanol
3: TFA / CH2Cl2 / 3 h / 20 °C
4: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr
View Scheme
ethyl 2-(hydroxyimino)-2-phenylacetate
131934-09-3, 135765-81-0, 712-41-4

ethyl 2-(hydroxyimino)-2-phenylacetate

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 85 percent / NaBH4; I2 / tetrahydrofuran / 4 h / Heating
2.1: dibenzoyl-L-tartaric acid / acetone / 6 h / 25 °C
2.2: aq. KOH / CH2Cl2
View Scheme
(4-Methoxy-phenyl)-[(S)-1-phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-amine
121411-08-3

(4-Methoxy-phenyl)-[(S)-1-phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-amine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C
2: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature
3: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min
4: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h
View Scheme
benzaldehyde
100-52-7

benzaldehyde

HI, I2

HI, I2

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 70 percent / DOWEX 50W X8-400 / benzene / Heating
2: LDA / tetrahydrofuran; hexane / -70 °C / 1.) 15 min, 2.) 30 min
3: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C
4: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature
5: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min
6: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h
View Scheme
Multi-step reaction with 3 steps
1: 4 Angstroem mol. sieves / CH2Cl2
2: TiCl4 / 15 °C / Irradiation
3: H2 / S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415.
View Scheme
4-methoxy-N-[(E)-phenylmethylidene]aniline
1613-90-7

4-methoxy-N-[(E)-phenylmethylidene]aniline

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LDA / tetrahydrofuran; hexane / -70 °C / 1.) 15 min, 2.) 30 min
2: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C
3: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature
4: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min
5: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h
View Scheme
(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethylamine
224433-92-5

(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethylamine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature
2: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min
3: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h
View Scheme
[(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester
224433-96-9

[(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min
2: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h
View Scheme
N-benzylidene-(S)-α-methylbenzylamine
69350-13-6

N-benzylidene-(S)-α-methylbenzylamine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TiCl4 / 15 °C / Irradiation
2: H2 / S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415.
View Scheme
1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LiH / dimethylformamide
2: H2NOH*HCl; NaOAc / ethanol; H2O
3: Fe / dimethylformamide
4: 100 percent / H2 / {1,2-bis[(R,R)-2,5-dimethylphospholane]benzene}rhodium(I) / toluene / 20 °C / 7600 Torr
5: 81 percent / methanol / Acid hydrolysis
View Scheme
With ω-transaminase from Arthrobacter; isopropylamine In tert-butyl methyl ether at 25℃; for 24h; Enzymatic reaction; enantioselective reaction;n/a
With (R)-1-phenyl-ethyl-amine; (R)-ω-transaminase from Mycobacterium vanbaalenii; NAD Enzymatic reaction; enantioselective reaction;
2-methoxymethoxy-1-phenyl-ethanone
103548-06-7

2-methoxymethoxy-1-phenyl-ethanone

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2NOH*HCl; NaOAc / ethanol; H2O
2: Fe / dimethylformamide
3: 100 percent / H2 / {1,2-bis[(R,R)-2,5-dimethylphospholane]benzene}rhodium(I) / toluene / 20 °C / 7600 Torr
4: 81 percent / methanol / Acid hydrolysis
View Scheme
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine
120417-13-2

(S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 41h; Substitution;100%
With dmap; triethylamine In dichloromethane at 20℃; for 12h;85%
With dmap; triethylamine In dichloromethane at 20℃;85%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester
476187-10-7

(Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In methanol for 24h; Heating;100%
formaldehyd
50-00-0

formaldehyd

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(S)-2-(N,N-dimethylamino)-2-phenylethanol
95977-53-0

(S)-2-(N,N-dimethylamino)-2-phenylethanol

Conditions
ConditionsYield
With HCOOH (98percent) In water for 18h; Heating;100%
4-(4-chlorophenyl)-4-oxobutanoic acid
3984-34-7

4-(4-chlorophenyl)-4-oxobutanoic acid

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(3S,7aS)-7a-(4-Chloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
873577-48-1

(3S,7aS)-7a-(4-Chloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Conditions
ConditionsYield
In toluene for 16h; Heating;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

4-(2,4-dichlorophenyl)-4-oxobutanoic acid
58457-57-1

4-(2,4-dichlorophenyl)-4-oxobutanoic acid

(3S,7aS)-7a-(2,4-Dichloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
808186-29-0

(3S,7aS)-7a-(2,4-Dichloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Conditions
ConditionsYield
In toluene for 16h; Heating;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

4-(2,4-difluorophenyl)-4-oxobutanoic acid
110931-77-6

4-(2,4-difluorophenyl)-4-oxobutanoic acid

(3S,7aS)-7a-(2,4-Difluoro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
808186-32-5

(3S,7aS)-7a-(2,4-Difluoro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

Conditions
ConditionsYield
In toluene for 16h; Heating;100%
2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

2-{(E)-((1S)-2-hydroxy-1-phenylethylimino)methyl}phenol
113866-46-9, 129049-04-3, 129049-05-4

2-{(E)-((1S)-2-hydroxy-1-phenylethylimino)methyl}phenol

Conditions
ConditionsYield
With sodium sulfate In methanol for 12h; Heating;100%
In ethanol at 20℃;
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

ethyl 5-formyl-3-methoxy-4-methyl-1H-pyrrole-2-carboxylate
15431-67-1

ethyl 5-formyl-3-methoxy-4-methyl-1H-pyrrole-2-carboxylate

ethyl 4-methyl-3-methoxy-5-[(L-phenylglycinolimino)methyl]-1H-pyrrole-2-carboxylate

ethyl 4-methyl-3-methoxy-5-[(L-phenylglycinolimino)methyl]-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane100%
(3E,5E)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[2-oxo-eth-(Z)-ylidene]-hepta-3,5-dienoic acid ethyl ester

(3E,5E)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[2-oxo-eth-(Z)-ylidene]-hepta-3,5-dienoic acid ethyl ester

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

5-[3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-3-phenyl-2,3,6,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-7-carboxylic acid ethyl ester

5-[3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-3-phenyl-2,3,6,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-7-carboxylic acid ethyl ester

Conditions
ConditionsYield
In chloroform-d1 at 24℃;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

ethyl (E,E)-4-oxo-2-styrylbut-2-enoate
344907-95-5

ethyl (E,E)-4-oxo-2-styrylbut-2-enoate

3,5-diphenyl-2,3,6,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-7-carboxylic acid ethyl ester

3,5-diphenyl-2,3,6,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-7-carboxylic acid ethyl ester

Conditions
ConditionsYield
In chloroform-d1 at 24℃;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

acrolein
107-02-8

acrolein

(3S,9S)-3,9-diphenyloctahydro-5H,11H-bis[1,3]oxazolo[3,2-a:3',2'-e][1,5]diazocine
1055874-41-3

(3S,9S)-3,9-diphenyloctahydro-5H,11H-bis[1,3]oxazolo[3,2-a:3',2'-e][1,5]diazocine

Conditions
ConditionsYield
In chloroform at 20℃; for 0.0833333h;100%
In toluene at 20℃; for 15h; Molecular sieve;36%
hex-5-en-1-al
764-59-0

hex-5-en-1-al

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(4S)-2-(pent-4-en-1-yl)-4-phenyloxazolidine

(4S)-2-(pent-4-en-1-yl)-4-phenyloxazolidine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane Inert atmosphere;100%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

C49H61O2P

C49H61O2P

C57H70NO2P

C57H70NO2P

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate
117049-14-6

tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h; Acylation;99%
In chloroform at 0 - 20℃;97%
With triethylamine In tetrahydrofuran for 2h;96%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]
182966-70-7

(4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

Conditions
ConditionsYield
at 120℃; for 3h;99%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(S)-2-Phenyl-2-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-ethanol

(S)-2-Phenyl-2-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-ethanol

Conditions
ConditionsYield
In diethyl ether for 1.33333h; Ambient temperature;99%
carbon disulfide
75-15-0

carbon disulfide

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(S)-4-phenyl-1,3-oxazolidine-2-thione
190970-57-1

(S)-4-phenyl-1,3-oxazolidine-2-thione

Conditions
ConditionsYield
With dihydrogen peroxide; potassium carbonate In ethanol at 50℃;99%
Stage #1: carbon disulfide; (2S)-2-phenylglycinol With triethylamine In methanol at 20℃; for 0.5h;
Stage #2: With dihydrogen peroxide In methanol
95%
With dihydrogen peroxide; potassium carbonate In ethanol at 50℃; for 0.0833333h;80%
2-methoxy-6-methyl-benzaldehyde
54884-55-8

2-methoxy-6-methyl-benzaldehyde

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(+)-(βS)-β-{[(1E)-(2-methoxy-6-methylphenyl)methylene]amino}benzeneethanol
702684-35-3

(+)-(βS)-β-{[(1E)-(2-methoxy-6-methylphenyl)methylene]amino}benzeneethanol

Conditions
ConditionsYield
With 4A MS In ethanol at 20℃; for 26h;99%
(R)-1,1'-spirobiindane-7,7'-dicaboxylic acid
920985-42-8, 856407-39-1

(R)-1,1'-spirobiindane-7,7'-dicaboxylic acid

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(Ra,S,S)-N,N'-bis(2-hydroxy-1-phenylethyl)-1,1'-spirobiindane-7,7'-diamide

(Ra,S,S)-N,N'-bis(2-hydroxy-1-phenylethyl)-1,1'-spirobiindane-7,7'-diamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at -5 - 20℃;99%
trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

glyoxalic acid monohydrate
6000-59-5

glyoxalic acid monohydrate

D-homophenylalanine
82795-51-5

D-homophenylalanine

Conditions
ConditionsYield
In dichloromethane99%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

C14H18O3

C14H18O3

Conditions
ConditionsYield
In toluene at 20℃; for 4h; Molecular sieve;99%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2-hydroxy-1-phenylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester
215178-44-2

(2-hydroxy-1-phenylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions
ConditionsYield
In 1,4-dioxane; water at 20℃; for 16h;99%
(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

formic acid ethyl ester
109-94-4

formic acid ethyl ester

(+)-(2S)-2-(formylamino)-2-phenylethanol

(+)-(2S)-2-(formylamino)-2-phenylethanol

Conditions
ConditionsYield
Reflux;99%
3,3-dimethylglutaric anhydride
4160-82-1

3,3-dimethylglutaric anhydride

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

3-(((S)-2-hydroxy-1-phenylethyl-carbamoyl)methyl)-3-methylbutanoic acid
1327278-20-5

3-(((S)-2-hydroxy-1-phenylethyl-carbamoyl)methyl)-3-methylbutanoic acid

Conditions
ConditionsYield
In dichloromethane; toluene at 20 - 60℃; for 5.5h;99%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

(S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide

(S)-4-bromo-N-(2-hydroxy-1-phenylethyl)benzamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 25℃; for 20h; Solvent; chemoselective reaction;99%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 20h;60%
2-amino-3-pyridinecarbonitrile
24517-64-4

2-amino-3-pyridinecarbonitrile

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

3-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine-2-amine

3-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine-2-amine

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene at 60℃; for 96h; Inert atmosphere;99%

20989-17-7Relevant articles and documents

Enantioselective liquid-liquid extraction of (R,S)-phenylglycinol using a bisnaphthyl phosphoric acid derivative as chiral extractant

Schuur, Boelo,Verkuijl, Bastiaan J.V.,Bokhove, Jeroen,Minnaard, Adriaan J.,De Vries, Johannes G.,Heeres, Hero J.,Feringa, Ben L.

, p. 462 - 470 (2011)

This study demonstrates that enantioseparation by liquid-liquid extraction can be done in a continuous flow mode on both laboratory and industrial scale and is a promising technique that could become a competitive alternative for crystallization or chromatographic approaches. We studied the enantioselective liquid-liquid extraction of phenylglycinol (Pgl) using a bisnaphthyl phosphoric acid extractant. Batch experiments were performed to estimate extraction model parameters. The system was described using an extraction mechanism with homogeneous organic phase complexation. The complexation constants were very large, in the order of 108-1010 L/mol in the temperature range 279T303 K. The developed model was then used to design a multistage countercurrent extraction process with Centrifugal Contactor Separator (CCS) equipment. This study demonstrates that high purity (70% ee) with a reasonable yield (36%) can be obtained for a moderately selective system (α=1.7) with only six extraction stages. The technology is potentially applicable to a wide range of racemates. Copyright

Construction and activity evaluation of novel dual-target (SE/CYP51) anti-fungal agents containing amide naphthyl structure

An, Yunfei,Fan, Haiyan,Han, Jun,Liu, Wenxia,Liu, Yating,Sun, Bin,Sun, Zhuang

, (2021/11/16)

With the increase of fungal infection and drug resistance, it is becoming an urgent task to discover the highly effective antifungal drugs. In the study, we selected the key ergosterol bio-synthetic enzymes (Squalene epoxidase, SE; 14 α-demethylase, CYP51) as dual-target receptors to guide the construction of novel antifungal compounds, which could achieve the purpose of improving drug efficacy and reducing drug-resistance. Three different series of amide naphthyl compounds were generated through the method of skeleton growth, and their corresponding target products were synthesized. Most of compounds displayed the obvious biological activity against different Candida spp. and Aspergillus fumigatus. Among of them, target compounds 14a-2 and 20b-2 not only possessed the excellent broad-spectrum anti-fungal activity (MIC50, 0.125–2 μg/mL), but also maintained the anti-drug-resistant fungal activity (MIC50, 1–4 μg/mL). Preliminary mechanism study revealed the compounds (14a-2, 20b-2) could block the bio-synthetic pathway of ergosterol by inhibiting the dual-target (SE/CYP51) activity, and this finally caused the cleavage and death of fungal cells. In addition, we also discovered that compounds 14a-2 and 20b-2 with low toxic and side effects could exert the excellent therapeutic effect in mice model of fungal infection, which was worthy for further in-depth study.

Preparation method of oxazolidinone compound

-

, (2021/11/10)

The preparation method comprises the following steps 1): dissolving aromatic amino acid in methanol, dissolving the aromatic amino acid in methanol, heating up to 50 - 60 °C heat preservation 1 - 2h, 2) reducing: adding a catalytic amount of lithium salt in ethanol water as a solvent. 3) Ring-closing: toluene is used as a solvent, a reduction product and diethyl carbonate are added to 100 °C, a sodium methoxide solution is added dropwise, and the product is obtained after completion of the dropwise addition and after-treatment and purification after completion of the normal pressure distillation to the temperature of 100 °C heat preservation. The lithium salt is introduced to participate in the reaction, sodium borohydride is selected as a solvent, sodium borohydride is completely dissolved, and the lithium salt can be free from the compound to improve the reaction activity, so that the use amount of sodium borohydride is reduced to 2 equivalent, and the production cost is remarkably reduced.

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