cleomiscosin A diacetate

Base Information

• Chemical Name: cleomiscosin A diacetate
• CAS No.: 90706-59-5
• Molecular Formula: C₂₄H₂₂O₁₀
• Molecular Weight: 470.433
• Mol file: 90706-59-5.mol

Synonyms:

Chemical Property of cleomiscosin A diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cleomiscosin A diacetate

There total 14 articles about cleomiscosin A diacetate 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: 97.0%

acetic anhydride (108-24-7) + cleomiscosin A (76948-72-6,121587-15-3) → cleomiscosin A diacetate (90706-59-5,121587-16-4,121884-17-1)

Guidance literature:

With pyridine; at 100 ℃; for 1h;

DOI:10.1248/cpb.33.3218

Reference yield: 45.0%

acetic anhydride (108-24-7) + cleomiscosin A (76948-72-6,121587-15-3) → 5-nitrocleomiscosin A 4',9'-diacetate + cleomiscosin A diacetate (90706-59-5,121587-16-4,121884-17-1)

Guidance literature:

With sulfuric acid; nitric acid; at 20 ℃; for 5h;

DOI:10.1016/j.ejmech.2010.08.027

Reference yield:

7,8-dihydroxy-6-methoxy-2H-1-benzopyran-2-one (574-84-5) → cleomiscosin A diacetate (90706-59-5,121587-16-4,121884-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / 1.NaH / tetrahydrofuran; dimethylformamide / 1. room temp., 1 h; 2.) room temp. 3 h

2: 98 percent / tert-BuOK / dimethylformamide / 1. room temp., 1 h; 2.) room temp. 3 h

3: 99 percent / 2 N HCl-MeOH / 0.5 h / Ambient temperature

4: LiBH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

5: 5percent sulfuric acid / 60 °C

6: 5percent sulfuric acid / 60 °C

7: 96 percent / 1percent NaOH / methanol / 0.5 h / 0 °C

8: 97 percent / pyridine / 1 h / 100 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium borohydride; sulfuric acid; potassium tert-butylate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.3218

upstream raw materials:

acetic anhydride

Cleomiscosin A

cleomiscosin A

7,8-dihydroxy-6-methoxy-2H-1-benzopyran-2-one

Downstream raw materials:

cleomiscosin A monoacetate

Refernces

• 1、 Lin, Lee-Juian,Cordell, Geoffrey A.. "Synthesis and Structural Elucidation of Coumarinolignans". . p. 3052 - 3080. Retrieved 2007/10/02.
• 2、 Tanaka,Kato,Ito. "Total synthesis of cleomiscosin A, a coumarinolignoid". . p. 3218 - 3223. Retrieved 2007/10/02.