(-)-Porantheridine

Base Information

• Chemical Name: (-)-Porantheridine
• CAS No.: 39027-77-5
• Molecular Formula: C₁₅H₂₇NO
• Molecular Weight: 237.385
• Mol file: 39027-77-5.mol

Synonyms:2H-[1,3]Oxazino[2,3,4-de]quinolizine,decahydro-9a-methyl-2-propyl-, [2R-(2a,3ab,6aa,9ab)]-; (-)-Porantheridine; Porantheridine

Chemical Property of (-)-Porantheridine

Chemical Property:

• PSA: 12.47000
• LogP: 3.63650

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Isomeric with the preceding base, this alkaloid also occurs in POianthera coryrnbosa. It is a colourless laevorotatory gum which cannot be crystallized and has [edD - 26° (c 0.57, CHC13). The hydrobromide has m.p. l65-6°C and has been used for X-ray crystallographic analysis to determine the crystal structure.

Technology Process of (-)-Porantheridine

There total 37 articles about (-)-Porantheridine 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: 85.0%

C20H37NO4 → (+/-)-Porantheridin (39027-77-5,74957-81-6)

Guidance literature:

With oxygen; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield: 66.0%

(R)-1-{(2S,6S)-6-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-piperidin-2-yl}-pentan-2-ol (152005-78-2) → (-)-porantheridine (39027-77-5)

Guidance literature:

With 4 A molecular sieve; toluene-4-sulfonic acid; In benzene; for 6h; Heating;

DOI:10.1021/ja00072a053

Reference yield:

[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride (62026-31-7) → (-)-porantheridine (39027-77-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / CuBr, BF₃*OEt₂ / tetrahydrofuran / -78 °C

2: 1.) LDA / 1.) THF

3: 1.) Li₂CO₃, H₂, 2.) KOH / 1.) 5percent Pd/C / 1.) EtOAc, 1 atm, 2.) EtOH, reflux, 2 d

4: 66 percent / TsOH, 4A molecular sieves / benzene / 6 h / Heating

With potassium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; lithium carbonate; toluene-4-sulfonic acid; copper(I) bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; benzene;

DOI:10.1021/ja00072a053

upstream raw materials:

(R)-1-{(2S,6S)-6-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-piperidin-2-yl}-pentan-2-ol

ethyl 3-((trimethylsilyl)oxy)hex-2-enoate

(5S,8aS)-5-(2-oxo-pent-1-yl)hexahydrooxazolo-[3,4-a]pyridin-3-one

(5S,8aS)-5-[(2R)-(2-hydroxypentyl)]hexahydrooxazolo[3,4a]pyridin-3-one

Refernces

• 1、 David, Marc,Dhimane, Hamid,Vanucci-Bacqueì?, Corinne,Lhommet, Geì?rard. "Efficient total synthesis of enantiopure (-)-porantheridine". . p. 8402 - 8405. Retrieved 2007/10/03.
• 2、 Goessinger, Edda. "STEREOSELEKTIVE SYNTHESE VON (+/-)-PORANTHERIDIN". . p. 2229 - 2232. Retrieved 2007/10/02.