2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel

Base Information

• Chemical Name: 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel
• CAS No.: 222726-76-3
• Molecular Formula: C₅₅H₅₇NO₁₅
• Molecular Weight: 972.055
• Mol file: 222726-76-3.mol

Synonyms:2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel

Chemical Property of 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel

There total 47 articles about 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel 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: 93.0%

2',3'-O,N-[(S)-(p-Methoxybenzylidene)]-7-O-(triethylsilyl)paclitaxel (202390-88-3) → taxol (33069-62-4) + 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel (222726-76-3)

Guidance literature:

With water; trifluoroacetic acid; at 0 ℃; for 0.333333h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

ethyl 4-bromo-4-pentenoate (35804-44-5) → 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel (222726-76-3)

Guidance literature:

Multi-step reaction with 38 steps

1.1: LiAlH₄ / tetrahydrofuran / 0.67 h / 0 °C

2.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

3.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

3.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

4.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

5.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 90 percent / MeONa / methanol / 1 h / 0 °C

7.1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C

8.1: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

9.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

10.1: 90 percent / PDC / CH₂Cl₂ / 16 h / 20 °C

11.1: s-BuLi / cyclohexane / 0.42 h / -23 °C

11.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C

12.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C

13.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C

14.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C

15.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂; acetonitrile / 1 h / 20 °C

16.1: 98 percent / PdCl₂; H₂O / dimethylformamide / 3.5 h / 20 °C

17.1: 71 percent / TiCl₂; LiAlH₄ / tetrahydrofuran / 0.33 h / 40 °C

18.1: Na; NH₃ / tetrahydrofuran / 2 h / -78 - -45 °C

19.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C

20.1: 100 percent / pyridine / CH₂Cl₂ / 1.17 h / -45 °C

21.1: 84 percent / DMAP / benzene / 10 h / 35 °C

22.1: HCl; H₂O / tetrahydrofuran / 10 h / 60 °C

23.1: pyridine / 0.67 h / 20 °C

24.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

25.1: DMAP / 4 h / 100 °C

25.2: DMAP / toluene / 4 h / 100 °C

26.1: P(OMe)3 / 5 h / 110 °C

27.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C

28.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C

29.1: 98 percent / pyridine / 0.17 h / -23 °C

30.1: 15 percent / CuBr; PhCO₃(t-Bu) / acetonitrile / 13 h / -23 °C

31.1: 92 percent / OsO₄; pyridine / diethyl ether / 17 h / 20 °C

32.1: 42 percent / DBU / toluene / 1.75 h / 50 °C

33.1: 91 percent / DMAP; pyridine / 13 h / 20 °C

34.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C

35.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C

36.1: 87 percent / pyridine / 0.5 h / 20 °C

37.1: 88 percent / DMAP; DPTC / toluene / 1 h / 73 °C

38.1: 7 percent / TFA; H₂O / 0.33 h / 0 °C

With pyridine; 1H-imidazole; aluminium hydride; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tert-Butyl peroxybenzoate; 4 A molecular sieve; Celite; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; water; tert.-butyl lithium; sec.-butyllithium; sodium methylate; sodium acetate; sodium; titanium chloride; potassium tri-sec-butyl-borohydride; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; Cinanserin hydrochloride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; palladium dichloride; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 1.1: Reduction / 2.1: Etherification / 3.1: Metallation / 3.2: Substitution / 3.3: Addition / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Cycloaddition / 7.1: Reduction / 8.1: Etherification / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Metallation / 11.2: Alkylation / 12.1: Substitution / 13.1: Etherification / 14.1: Methylation / 15.1: Oxidation / 16.1: Oxidation / 17.1: Cyclization / 18.1: Substitution / 19.1: Substitution / 20.1: Acylation / 21.1: Acetylation / 22.1: Hydrolysis / 23.1: Etherificat;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

4-bromopent-4-en-1-ol (64180-78-5) → 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]paclitaxel (222726-76-3)

Guidance literature:

Multi-step reaction with 37 steps

1.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 0 °C

2.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

2.2: CuCN / diethyl ether; pentane / 0.5 h / 0 °C

2.3: 92 percent / diethyl ether; pentane / 1.33 h / -23 °C

3.1: 97 percent / HCl; H₂O / tetrahydrofuran / 0.83 h / 0 °C

4.1: 92 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

5.1: 90 percent / MeONa / methanol / 1 h / 0 °C

6.1: 94 percent / AlH₃ / toluene; tetrahydrofuran / 2 h / -78 °C

7.1: 100 percent / CSA / CH₂Cl₂ / 1 h / 20 °C

8.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

9.1: 90 percent / PDC / CH₂Cl₂ / 16 h / 20 °C

10.1: s-BuLi / cyclohexane / 0.42 h / -23 °C

10.2: 96 percent / cyclohexane; benzene / 1 h / 0 °C

11.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 50 °C

12.1: 99 percent / imidazole / dimethylformamide / 0.25 h / 20 °C

13.1: 96 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; diethyl ether / 0.5 h / -78 °C

14.1: 80 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂; acetonitrile / 1 h / 20 °C

15.1: 98 percent / PdCl₂; H₂O / dimethylformamide / 3.5 h / 20 °C

16.1: 71 percent / TiCl₂; LiAlH₄ / tetrahydrofuran / 0.33 h / 40 °C

17.1: Na; NH₃ / tetrahydrofuran / 2 h / -78 - -45 °C

18.1: TBAF / tetrahydrofuran / 0.08 h / 20 °C

19.1: 100 percent / pyridine / CH₂Cl₂ / 1.17 h / -45 °C

20.1: 84 percent / DMAP / benzene / 10 h / 35 °C

21.1: HCl; H₂O / tetrahydrofuran / 10 h / 60 °C

22.1: pyridine / 0.67 h / 20 °C

23.1: 76 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

24.1: DMAP / 4 h / 100 °C

24.2: DMAP / toluene / 4 h / 100 °C

25.1: P(OMe)3 / 5 h / 110 °C

26.1: 78 percent / PCC; Celite; NaOAc / benzene / 11 h / 95 °C

27.1: 87 percent / K-Selectride / tetrahydrofuran / 4 h / -23 °C

28.1: 98 percent / pyridine / 0.17 h / -23 °C

29.1: 15 percent / CuBr; PhCO₃(t-Bu) / acetonitrile / 13 h / -23 °C

30.1: 92 percent / OsO₄; pyridine / diethyl ether / 17 h / 20 °C

31.1: 42 percent / DBU / toluene / 1.75 h / 50 °C

32.1: 91 percent / DMAP; pyridine / 13 h / 20 °C

33.1: 94 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -78 °C

34.1: 96 percent / HF*pyridine / tetrahydrofuran / 1 h / 20 °C

35.1: 87 percent / pyridine / 0.5 h / 20 °C

36.1: 88 percent / DMAP; DPTC / toluene / 1 h / 73 °C

37.1: 7 percent / TFA; H₂O / 0.33 h / 0 °C

With pyridine; 1H-imidazole; aluminium hydride; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tert-Butyl peroxybenzoate; 4 A molecular sieve; Celite; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; water; tert.-butyl lithium; sec.-butyllithium; sodium methylate; sodium acetate; sodium; titanium chloride; potassium tri-sec-butyl-borohydride; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; Cinanserin hydrochloride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; palladium dichloride; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution / 2.3: Addition / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Cycloaddition / 6.1: Reduction / 7.1: Etherification / 8.1: Hydrolysis / 9.1: Oxidation / 10.1: Metallation / 10.2: Alkylation / 11.1: Substitution / 12.1: Etherification / 13.1: Methylation / 14.1: Oxidation / 15.1: Oxidation / 16.1: Cyclization / 17.1: Substitution / 18.1: Substitution / 19.1: Acylation / 20.1: Acetylation / 21.1: Hydrolysis / 22.1: Etherification / 23.1: Oxidat;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

upstream raw materials:

2',3'-O,N-[(S)-(p-Methoxybenzylidene)]-7-O-(triethylsilyl)paclitaxel

4-bromopent-4-en-1-ol

ethyl 4-bromo-4-pentenoate

baccatin III

Downstream raw materials:

taxol

Refernces