13-deoxybaccatin III

Base Information

• Chemical Name: 13-deoxybaccatin III
• CAS No.: 155588-14-0
• Molecular Formula: C₃₁H₃₈O₁₀
• Molecular Weight: 570.637

Synonyms:13-deoxybaccatin III

Chemical Property of 13-deoxybaccatin III

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 13-deoxybaccatin III

There total 64 articles about 13-deoxybaccatin III 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: 65.0%

(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate (155588-13-9) → 13-deoxybaccatin III (155588-14-0)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; for 1h;

DOI:10.1039/c39940000295

Reference yield:

(2R,4aR,8aS)-4a,7,8,8a-tetrahydro-5-iodo-4a-methyl-1-phenyl-4H-benzo[d][1,3]dioxine (815577-89-0) → 13-deoxybaccatin III (155588-14-0)

Guidance literature:

Multi-step reaction with 25 steps

1.1: diisobutylaluminium hydride / dichloromethane / 24 h / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: tert.-butylhydroperoxide; vanadium(V) oxytriethoxide / toluene / 1 h / 0 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere

6.1: hydrogenchloride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

9.1: tetrahydrofuran; diethyl ether / 6 h / 0 °C / Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phenolate / toluene / 3 h / 100 °C / Inert atmosphere

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 50 °C / Inert atmosphere

13.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 4 h / 20 °C / Inert atmosphere

14.1: zinc; lead(II) chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

14.2: 3 h / 0 °C / Inert atmosphere

15.1: selenium(IV) oxide / 1,4-dioxane / 2 h / 40 °C / Inert atmosphere

16.1: N,N,N,N,-tetramethylethylenediamine; osmium(VIII) oxide / dichloromethane / 2 h / -40 °C / Inert atmosphere

17.1: sodium dithionite / tetrahydrofuran; water / 16 h / -40 °C / Inert atmosphere

18.1: pyridine / dichloromethane / 1 h / -40 °C / Inert atmosphere

19.1: dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere

20.1: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere

21.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 1 h / 100 °C / Inert atmosphere

22.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

22.2: 1.5 h / 0 °C / Inert atmosphere

23.1: dmap; triethylamine / toluene / 8 h / Inert atmosphere; Reflux

23.2: 24 h / Inert atmosphere; Reflux

24.1: tert.-butylhydroperoxide; ruthenium trichloride / water; 1,2-dichloro-ethane; decane / 3.5 h / 0 °C / Inert atmosphere

25.1: 10 wt% Pd(OH)2 on carbon; hydrogen / 0.17 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; dmap; selenium(IV) oxide; ruthenium trichloride; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium dithionite; N,N,N,N,-tetramethylethylenediamine; 10 wt% Pd(OH)2 on carbon; boron trifluoride diethyl etherate; potassium phenolate; tetrabutyl ammonium fluoride; hydrogen; vanadium(V) oxytriethoxide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lead(II) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; decane; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; 4.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1002/chem.201404295

Reference yield:

(2R,3S)-3-hydroxy-2-hydroxymethyl-2-methylcyclohexanone (619335-75-0) → 13-deoxybaccatin III (155588-14-0)

Guidance literature:

Multi-step reaction with 28 steps

1.1: C₉H₁₆O₃S / dichloromethane / 3 h / Inert atmosphere

2.1: triethylamine; hydrazine / ethanol / 48 h / 130 °C / Sealed tube; Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; iodine / diethyl ether; benzene / 0.75 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane / 24 h / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: tert.-butylhydroperoxide; vanadium(V) oxytriethoxide / toluene / 1 h / 0 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere

9.1: hydrogenchloride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

12.1: tetrahydrofuran; diethyl ether / 6 h / 0 °C / Inert atmosphere

13.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

14.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phenolate / toluene / 3 h / 100 °C / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 13 h / 50 °C / Inert atmosphere

16.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 4 h / 20 °C / Inert atmosphere

17.1: zinc; lead(II) chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

17.2: 3 h / 0 °C / Inert atmosphere

18.1: selenium(IV) oxide / 1,4-dioxane / 2 h / 40 °C / Inert atmosphere

19.1: N,N,N,N,-tetramethylethylenediamine; osmium(VIII) oxide / dichloromethane / 2 h / -40 °C / Inert atmosphere

20.1: sodium dithionite / tetrahydrofuran; water / 16 h / -40 °C / Inert atmosphere

21.1: pyridine / dichloromethane / 1 h / -40 °C / Inert atmosphere

22.1: dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere

23.1: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere

24.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 1 h / 100 °C / Inert atmosphere

25.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

25.2: 1.5 h / 0 °C / Inert atmosphere

26.1: dmap; triethylamine / toluene / 8 h / Inert atmosphere; Reflux

26.2: 24 h / Inert atmosphere; Reflux

27.1: tert.-butylhydroperoxide; ruthenium trichloride / water; 1,2-dichloro-ethane; decane / 3.5 h / 0 °C / Inert atmosphere

28.1: 10 wt% Pd(OH)2 on carbon; hydrogen / 0.17 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; dmap; selenium(IV) oxide; ruthenium trichloride; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium dithionite; N,N,N,N,-tetramethylethylenediamine; 10 wt% Pd(OH)2 on carbon; boron trifluoride diethyl etherate; C₉H₁₆O₃S; potassium phenolate; tetrabutyl ammonium fluoride; hydrogen; iodine; vanadium(V) oxytriethoxide; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lead(II) chloride; hydrazine; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; decane; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; benzene; 7.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1002/chem.201404295

upstream raw materials:

(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

7-(triethylsilyl)baccatin III

C₄₁H₅₄N₂O₁₁SSi

(2R,4aR,8aS)-4a,7,8,8a-tetrahydro-5-iodo-4a-methyl-1-phenyl-4H-benzo[d][1,3]dioxine

Downstream raw materials:

(2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate

7-O-triethylsilyl-13-keto baccatin III

13β-bromo-13-deoxy-7-O-(triethylsilyl)baccatin III

13-epi-7-O-(triethylsilyl)baccatin III

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