8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 800388-86-7
• Molecular Formula: C₅₆H₇₆N₄O₈SeSi₂
• Molecular Weight: 1068.37
• Mol file: 800388-86-7.mol

Synonyms:8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

There total 24 articles about 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

7-{1-[1-(1-allyloxycarbonyl-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester (800388-84-5) → 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester (800388-86-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; In dichloromethane; at -45 - 0 ℃; for 0.583333h;

DOI:10.1021/ja0529337

Reference yield:

quinoline-2-carboxylic acid (93-10-7,1199266-78-8) → 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester (800388-86-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / SOCl₂ / 6 h / 60 °C

2.1: 60 percent / PtO₂; trifluoroacetic acid; H₂ / 5 h / 25 °C / 2844.31 Torr

3.1: 99 percent / FeSO₄*7H₂O; aq. H₂O₂; TFA / air / 2 h / 0 °C

4.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol; B(OMe)3; BH3*SMe2 / tetrahydrofuran / 0.5 h / 0 °C

5.1: Et₃N / CH₂Cl₂ / 3 h / 25 °C

6.1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 12 h / 25 °C

7.1: CH₂Cl₂ / 14 h / 0 - 25 °C

8.1: aq. K₂CO₃ / CH₂Cl₂ / 6 h / 25 °C

9.1: Burgess reagent / tetrahydrofuran / 0.33 h / 25 °C

10.1: Katsuki catalyst; 4-phenylpyridine N-oxide; NaOCl / CH₂Cl₂; aq. phosphate buffer / 1 h / 25 °C / pH 11.5

11.1: N-bromosuccinimide; 2,2'-azabisisobutyronitrile / CCl₄ / 0.5 h / 80 °C

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 25 °C

13.1: 36 mg / LiClO₄ / acetonitrile / 22 h / 60 °C

14.1: 94 percent / i-Pr₂NEt / tetrahydrofuran / 3 h / 0 - 25 °C

15.1: aq. NaOH / methanol / 5.5 h / 0 - 25 °C

16.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 4 h / 25 °C

16.2: 64 percent / 4-dimethylaminopyridine / toluene / 14 h / 25 °C

17.1: PdCl₂(PPh₃)2; n-Bu₃SnH / CH₂Cl₂ / 1 h / 0 °C

18.1: 250 mg / 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆ / dimethylformamide / 1 h / 25 - 40 °C / sonication

19.1: 100 percent / n-Bu₃SnH; PdCl₂(PPh₃)2 / CH₂Cl₂ / 0.58 h / -45 - 0 °C

With platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium hypochlorite; N-Bromosuccinimide; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; 4-Phenylpyridine 1-oxide; Burgess Reagent; Trimethyl borate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; Katsuki catalyst; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; lithium perchlorate; potassium carbonate; (R)-α,α-diphenylprolinol; iron(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; HATU; trifluoroacetic acid; air; In tetrahydrofuran; methanol; tetrachloromethane; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 16.2: Yamaguchi-type esterification;

DOI:10.1021/ja0529337

Reference yield:

quinoline-2-carboxylic acid methyl ester (19575-07-6) → 8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-{1-[1-(1-carboxy-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester (800388-86-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 60 percent / PtO₂; trifluoroacetic acid; H₂ / 5 h / 25 °C / 2844.31 Torr

2.1: 99 percent / FeSO₄*7H₂O; aq. H₂O₂; TFA / air / 2 h / 0 °C

3.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol; B(OMe)3; BH3*SMe2 / tetrahydrofuran / 0.5 h / 0 °C

4.1: Et₃N / CH₂Cl₂ / 3 h / 25 °C

5.1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 12 h / 25 °C

6.1: CH₂Cl₂ / 14 h / 0 - 25 °C

7.1: aq. K₂CO₃ / CH₂Cl₂ / 6 h / 25 °C

8.1: Burgess reagent / tetrahydrofuran / 0.33 h / 25 °C

9.1: Katsuki catalyst; 4-phenylpyridine N-oxide; NaOCl / CH₂Cl₂; aq. phosphate buffer / 1 h / 25 °C / pH 11.5

10.1: N-bromosuccinimide; 2,2'-azabisisobutyronitrile / CCl₄ / 0.5 h / 80 °C

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 25 °C

12.1: 36 mg / LiClO₄ / acetonitrile / 22 h / 60 °C

13.1: 94 percent / i-Pr₂NEt / tetrahydrofuran / 3 h / 0 - 25 °C

14.1: aq. NaOH / methanol / 5.5 h / 0 - 25 °C

15.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 4 h / 25 °C

15.2: 64 percent / 4-dimethylaminopyridine / toluene / 14 h / 25 °C

16.1: PdCl₂(PPh₃)2; n-Bu₃SnH / CH₂Cl₂ / 1 h / 0 °C

17.1: 250 mg / 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆ / dimethylformamide / 1 h / 25 - 40 °C / sonication

18.1: 100 percent / n-Bu₃SnH; PdCl₂(PPh₃)2 / CH₂Cl₂ / 0.58 h / -45 - 0 °C

With platinum(IV) oxide; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium hypochlorite; N-Bromosuccinimide; 1-hydroxy-7-aza-benzotriazole; 4-Phenylpyridine 1-oxide; Burgess Reagent; Trimethyl borate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; Katsuki catalyst; 2,4,6-trichlorobenzoyl chloride; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; lithium perchlorate; potassium carbonate; (R)-α,α-diphenylprolinol; iron(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; HATU; trifluoroacetic acid; air; In tetrahydrofuran; methanol; tetrachloromethane; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 15.2: Yamaguchi-type esterification;

DOI:10.1021/ja0529337

upstream raw materials:

7-{1-[1-(1-allyloxycarbonyl-2-phenylselanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylamino}-8-(tert-butyl-dimethyl-silanyloxy)-4-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7,8-dihydro-quinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester

(R)-2-Amino-3-phenylselanyl-propionic acid allyl ester

(R)-2-((S)-2-Amino-propionylamino)-3-phenylselanyl-propionic acid allyl ester

(R)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-3-phenylselanyl-propionic acid allyl ester

Downstream raw materials:

C₁₃₄H₁₈₇N₁₉O₂₀S₅Se₃Si₅