29-Nor-20-oxolupeol

Base Information

• Chemical Name: 29-Nor-20-oxolupeol
• CAS No.: 19891-85-1
• Molecular Formula: C29H48O2
• Molecular Weight: 428.699
• Mol file: 19891-85-1.mol

Synonyms:29-Nor-20-oxolupeol;3beta-Hydroxy-30-norlupan-20-one

Chemical Property of 29-Nor-20-oxolupeol

Chemical Property:

• Melting Point: 237-239℃
• Boiling Point: 503.5±23.0 °C(Predicted)
• PKA: 15.18±0.70(Predicted)
• PSA: 37.30000
• Density: 1.015±0.06 g/cm3(Predicted)
• LogP: 7.03770

Purity/Quality:

99% ^*data from raw suppliers

29-Nor-20-oxolupeol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 29-Nor-20-oxolupeol

There total 12 articles about 29-Nor-20-oxolupeol 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: 6.0%

lupenol (545-47-1) → (20RS)-3β-hydroxylupan-29-al + lup-20(30)-ene-3β,29-diol (20065-99-0) + 3β-hydroxy-20-oxo-30-norlupane (19891-85-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 5 ℃; for 2h;

Reference yield: 3.0%

lupenol (545-47-1) + acetic acid (64-19-7,77671-22-8) → lupeol acetate (1617-68-1,6610-54-4,55870-40-1,74345-30-5,101627-42-3) + 3β-acetoxy-30-nor-lupan-20-one (55870-41-2) + 3β-hydroxy-20-oxo-30-norlupane (19891-85-1) + 1-(2-hydroxy-1-oxopropan-2-yl)-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl acetate

Guidance literature:

With oxone||potassium monopersulfate triple salt; at 100 ℃; for 3h;

DOI:10.1080/14786419.2020.1758095

Reference yield:

lupenol (545-47-1) → 3β-hydroxy-20-oxo-30-norlupane (19891-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; OsO₄ / 10 °C / Kochen des Reaktionsprodukts mit Na₂SO₃ in wss.-aethanol. Loesung

2: lead (IV)-acetate; acetic acid / 10 °C

With lead(IV) acetate; osmium(VIII) oxide; diethyl ether; acetic acid;

DOI:10.1039/jr9400000456

upstream raw materials:

(20RS)-lupane-3β,20,29-triol

3β-acetoxy-30-nor-lupan-20-one

29-Nor-19α-H-lupan-20-on-3β-yl-acetat

lupenol

Refernces

• 1、 Baddeley,G.V. et al.. "-". . p. 1173 - 1181. Retrieved 1964.
• 2、 Matsunaga, Shunyo,Tanaka, Reiko,Akagi, Masao. "TRITERPENOIDS FROM EUPHORBIA MACULATA". . p. 535 - 538. Retrieved 1988.
• 3、 Mishra, Namita,Kumar, Satish,Khare, Pritibha,Raj, Kanwal. "Novel class of hybrid natural products derived from lupeol (Part-Iii) pharmacomodulation on lupeol skeleton: Design, synthesis and biological evaluation of novel lupeol derivatives as antimalarial agents". . p. 97 - 110. Retrieved 2019/01/21.