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Cas Database

136088-21-6

136088-21-6

Identification

  • Product Name:2-Oxazolidinone, 3-[(2S,3S)-3-[(2-aminophenyl)thio]-2-[(2-methoxyethoxy)methoxy]-3-(4- methoxyphenyl)-1-oxopropyl]-4-(1-methylethyl)-, (4S)-

  • CAS Number: 136088-21-6

  • EINECS:

  • Molecular Weight:518.631

  • Molecular Formula: C26H34N2O7S

  • HS Code:

  • Mol File:136088-21-6.mol

Synonyms:

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Relevant articles and documentsAll total 2 Articles be found

Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem

Miyata, Okiko,Shinada, Tetsuro,Ninomiya, Ichiya,Naito, Takeaki

, p. 2421 - 2438 (2007/10/03)

A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to α,β-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem.

Asymmetric induction at two contiguous stereogenic centers by diastereoface differentiating nucleophilic addition reaction

Miyata, Okiko,Shinada, Tetsuro,Ninomiya, Ichiya,Naito, Takeaki

, p. 3519 - 3522 (2007/10/02)

Distereoface differentiating nucleophilic of thiophenol to olefins delivers a new concomitant asymmetric construction of two contiguous stereogenic centers and has been successfully applied to the asymmetric synthesis of (+)-diltiazem.

Process route upstream and downstream products

Process route

(S)-3-(2-methoxyethoxy)methyloxyacetyl-4-(1-methylethyl)-2-oxazolidinone
928007-17-4

(S)-3-(2-methoxyethoxy)methyloxyacetyl-4-(1-methylethyl)-2-oxazolidinone

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1.) LDA
2: Et3N
3: DBU
4: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
Multi-step reaction with 4 steps
1: 1.) LDA
2: Et3N
3: DBU
4: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
Multi-step reaction with 4 steps
1: LDA
2: Et3N
3: DBU
4: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
Multi-step reaction with 4 steps
1: LDA
2: Et3N
3: DBU
4: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
(S)-3-[3-Hydroxy-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
188686-10-4

(S)-3-[3-Hydroxy-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: Et3N
2: DBU
3: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
Multi-step reaction with 3 steps
1: Et3N
2: DBU
3: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
Multi-step reaction with 3 steps
1: Et3N
2: DBU
3: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran;
Multi-step reaction with 3 steps
1: Et3N
2: DBU
3: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran;
Methanesulfonic acid 3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2-(2-methoxy-ethoxymethoxy)-1-(4-methoxy-phenyl)-3-oxo-propyl ester

Methanesulfonic acid 3-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2-(2-methoxy-ethoxymethoxy)-1-(4-methoxy-phenyl)-3-oxo-propyl ester

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: DBU
2: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene;
Multi-step reaction with 2 steps
1: DBU
2: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene;
Multi-step reaction with 2 steps
1: DBU
2: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: DBU
2: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
(S)-4-Isopropyl-3-[(E)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one
136057-78-8

(S)-4-Isopropyl-3-[(E)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
With lithium o-aminothiophenoxide; In tetrahydrofuran; at -40 ℃; Yield given;
(S)-4-Isopropyl-3-[(Z)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one
136057-77-7

(S)-4-Isopropyl-3-[(Z)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
With lithium o-aminothiophenoxide; In tetrahydrofuran; at -40 ℃; Yield given;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: LDA
2: Et3N
3: DBU
4: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
Multi-step reaction with 4 steps
1: LDA
2: Et3N
3: DBU
4: lithium o-aminothiophenoxide / tetrahydrofuran / -40 °C
With lithium o-aminothiophenoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
(4S)-4-isopropyl-1,3-oxazolidin-2-one
17016-83-0

(4S)-4-isopropyl-1,3-oxazolidin-2-one

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 1.) n-BuLi / 1) THF, hexane, -78 deg C
2: 1.) LDA
3: Et3N
4: DBU
5: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
Multi-step reaction with 5 steps
1: 1.) n-BuLi / 1) THF, hexane, -78 deg C
2: 1.) LDA
3: Et3N
4: DBU
5: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 1.) LDA
2: Et3N
3: DBU
4: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
Multi-step reaction with 4 steps
1: 1.) LDA
2: Et3N
3: DBU
4: 1.) n-BuLi / 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h
With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
(S)-4-Isopropyl-3-[(E)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one
136057-78-8

(S)-4-Isopropyl-3-[(E)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h;
(S)-4-Isopropyl-3-[(Z)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one
136057-77-7

(S)-4-Isopropyl-3-[(Z)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-acryloyl]-oxazolidin-2-one

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one
136088-21-6

(S)-3-[(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

(S)-3-[(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions
Conditions Yield
With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) THF, hexane, -40 deg C; 2) THF, hexane, -40 deg C, 3 h;

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