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

Base Information

• Chemical Name: 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one
• CAS No.: 223798-14-9
• Molecular Formula: C₃₄H₄₄O₇
• Molecular Weight: 564.719
• Mol file: 223798-14-9.mol

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

Chemical Property of 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one

There total 4 articles about 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-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: 98.0%

chloromethyl methyl ether (107-30-2) + 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-hydroxytaxa-4(20),11-dien-13-one (172304-02-8) → 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one (223798-14-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 79 - 83 ℃; for 1h;

DOI:10.1021/np020240n

Reference yield:

taxinine (3835-52-7) → 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one (223798-14-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / aq. KOH / methanol; dioxane / 3 h / 0 - 20 °C

2: 97 percent / PPTS / CH₂Cl₂ / 1.5 h / 20 °C

3: 88 percent / aq. KOH / dioxane; methanol / 4.5 h / 0 - 20 °C

4: 98 percent / DIEA; DMAP / 1,2-dichloro-ethane / 1 h / 79 - 83 °C

With dmap; potassium hydroxide; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/np020240n

Reference yield:

9α,10β-dihydroxy-2α-acetoxy-5α-cinnamoyloxy-taxa-4(20),11-dien-13-one (15135-57-6) → 5α-cinnamoyloxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-13-one (223798-14-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / PPTS / CH₂Cl₂ / 1.5 h / 20 °C

2: 88 percent / aq. KOH / dioxane; methanol / 4.5 h / 0 - 20 °C

3: 98 percent / DIEA; DMAP / 1,2-dichloro-ethane / 1 h / 79 - 83 °C

With dmap; potassium hydroxide; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/np020240n

upstream raw materials:

chloromethyl methyl ether

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

taxinine

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