9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one

Base Information

• Chemical Name: 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one
• CAS No.: 477952-08-2
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.52
• Mol file: 477952-08-2.mol

Synonyms:9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one

Chemical Property of 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one

There total 1 articles about 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one 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: 88.0%

2α-acetoxy-5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)taxa-4(20),11-dien-13-one (2571-73-5) → 9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one (477952-08-2) + 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-hydroxytaxa-4(20),11-dien-13-one (172304-02-8)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; methanol; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/np020240n

Reference yield:

9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one (477952-08-2) → 5β-benzoyloxy-2α,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / 2,6-lutidine / CHCl₃ / 2 h / -20 °C

2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C

3: KOH / ethanol / 6 h / 20 °C

4: 92 percent / OsO₄; NMO; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 0 °C

5: 82 percent / imidazole / dimethylformamide / 3 h / 20 °C

6: 86 percent / pyridine / 24 h / 20 °C

7: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8: 65 percent / DBU / toluene / 1 h / Heating

9: 0.3 percent HCl / methanol / 0.42 h / 0 °C

10: 24 percent / DCC; DMAP / acetonitrile / 24 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; potassium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(03)00048-6

Reference yield:

9α,10β-(dimethylmethylenedioxy)-2α,2α-dihydroxytaxa-4(20),11-dien-13-one (477952-08-2) → 9α,10β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-11-taxen-13-one (532935-96-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / 2,6-lutidine / CHCl₃ / 2 h / -20 °C

2: p-toluenesulfonic acid / tetrahydrofuran / 2 h / 20 °C

3: KOH / ethanol / 6 h / 20 °C

4: 92 percent / OsO₄; NMO; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 0 °C

5: 82 percent / imidazole / dimethylformamide / 3 h / 20 °C

6: 86 percent / pyridine / 24 h / 20 °C

7: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8: 65 percent / DBU / toluene / 1 h / Heating

9: 0.3 percent HCl / methanol / 0.42 h / 0 °C

10: 65 percent / DCC; DMAP / acetonitrile / 24 h / 0 °C

11: 66 percent / AcOH; H₂O / tetrahydrofuran / 29 h / 52 °C

12: 100 percent / pyridine / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; potassium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(03)00048-6

upstream raw materials:

2α-acetoxy-5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)taxa-4(20),11-dien-13-one

Downstream raw materials:

2α-benzoyloxy-5β,20-epoxy-4α,9α,10β-trihydroxy-11-taxen-13-one

2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-9α,10β-isopropylidenedioxy-11-taxen-13-one

9α,10β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-4α-hydroxy-11-taxen-13-one