21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1α,12α,15β-triol 15-acetate

Base Information

• Chemical Name: 21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1α,12α,15β-triol 15-acetate
• CAS No.: 5008-49-1
• Molecular Formula: C₂₄H₃₅NO₄
• Molecular Weight: 401.546
• Mol file: 5008-49-1.mol

Synonyms:

Chemical Property of 21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1α,12α,15β-triol 15-acetate

Chemical Property:

• Melting Point: 170-10C
• PSA: 70.00000
• LogP: 2.30050

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This atisine alkaloid, obtained from Aconitum lucidusculum and A. yeosoensis, was originally given the empirical formula C24H3704N, later changed to that given above. The base crystallizes in colourless leaflets from MeOH and has [α]D- 95.5° (CHCI3). All of the salts crystallize well: the hydrochloride monohydrate, m.p. 98-115°C or 245-265°C (dry, dec.); the hydrobromide, m.p. 248-2500C; [α]20D - 62.7° (H20); the hydriodide as orthorhombic crystals, m.p. 249-2500C; perchlorate decomposing at 260-5°C; [α]15D - 70.3° (EtOH); methiodide, m.p. 197°C; [α]15D - 65° (EtOH) and the picrate, m.p. 173-6°C. The alkaloid contains a secondary and a tertiary hydroxyl group and forms the monoacetate as the crystalline trihydrate, m.p. 113-7°C or 139-144°C (dry); [α]15D- 50.4° (H20). On alkaline hydrolysis, the alkaloid yields acetic acid and Luciduline (q.v.).

Technology Process of 21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1α,12α,15β-triol 15-acetate

There total 1 articles about 21-Ethyl-4-methyl-16-methylene-7,20-cycloveatchane-1α,12α,15β-triol 15-acetate 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:

→ Lucidusculin (5008-49-1,137120-52-6)

Guidance literature:

Lucidusculin, N-Bromsuccinimid / Bzl., Δ;

DOI:10.1246/bcsj.33.644

Reference yield: 95.0%

benzoyl chloride (98-88-4) + lucidusculine (5008-49-1,137120-52-6) → 12-benzoyllucidusculine

Guidance literature:

With pyridine; at 0 ℃; for 1h;

DOI:10.1248/cpb.48.1065

Reference yield:

12-epi-lucidusculine (5008-49-1,137120-52-6) → C37H43NO5 (137038-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 5percent KOH / H₂O; methanol

2: 57 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

3: 70 percent / dimethylaminopyridine, pyridine

4: 78 percent / HF-pyridine / tetrahydrofuran

5: 27 percent / BF₃-Et₂O / 6.5 h / Ambient temperature

With pyridine; dmap; potassium hydroxide; boron trifluoride diethyl etherate; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1248/cpb.39.1644

Downstream raw materials:

12-epi-napelline

C₃₆H₄₁NO₅

C₃₇H₄₃NO₅

C₄₂H₅₅NO₅Si