D/E-trans-Ψ-vincadifformine

Base Information

• Chemical Name: D/E-trans-Ψ-vincadifformine
• CAS No.: 91740-14-6
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.45
• Mol file: 91740-14-6.mol

Synonyms:

Chemical Property of D/E-trans-Ψ-vincadifformine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D/E-trans-Ψ-vincadifformine

There total 17 articles about D/E-trans-Ψ-vincadifformine 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: 43.0%

21-Thioxo-14-epipseudovincadifformine → (+/-)-14-Epipseudovincadifformine (26251-92-3,40294-53-9,56815-95-3,56942-56-4,73836-92-7,73837-57-7,91740-14-6,106621-38-9,121153-93-3)

Guidance literature:

With nickel; In tetrahydrofuran;

DOI:10.1021/jo00074a039

Reference yield:

D/E-trans-20,21-didehydro-Ψ-vincadifformine (139133-18-9) → D/E-trans-Ψ-vincadifformine (26251-92-3,40294-53-9,56815-95-3,56942-56-4,73836-92-7,73837-57-7,91740-14-6,106621-38-9,121153-93-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; under 760 Torr; Yield given;

DOI:10.1021/jo00032a029

Reference yield:

2,16-Didehydro-16,20-bis(methoxycarbonyl)-21-phenyl-20,21-seco-pseudoaspidospermidine (3α,14β,20αβ) (109704-78-1,121153-56-8,121155-14-4) → (+/-)-14-Epipseudovincadifformine (26251-92-3,40294-53-9,56815-95-3,56942-56-4,73836-92-7,73837-57-7,91740-14-6,106621-38-9,121153-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) H₂, 2.) p-toluenesulfonic acid monohydrate / 1.) 10percent Pd/C / 1.) glacial acetic acid, 40 min, 2.) toluene, reflux, 16 h

2: 71 percent / P₄S₁₀ / tetrahydrofuran / 24 h / Ambient temperature

3: 43 percent / Raney-Ni / tetrahydrofuran

With tetraphosphorus decasulfide; hydrogen; nickel; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo00074a039

upstream raw materials:

(R)-4-[(S)-2-(Toluene-4-sulfonyloxymethyl)-butyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

2,16-Didehydro-16,20-bis(methoxycarbonyl)-21-phenyl-20,21-seco-pseudoaspidospermidine (3α,14β,20αβ)

N^b-benzyl-21-hydroxy-D-seco-Ψ-vincadifformine

N^b-benzyl-21-(tosyloxy)-D-seco-Ψ-vincadifformine

Refernces

• 1、 Kalaus, Gyoergy,Greiner, Istvan,Kajtar-Peredy, Maria,Brlik, Janos,Szabo, Lajos,Szantay, Csaba. "Synthesis of Vinca Alkaloids and Related Compounds. 64. Total Syntheses of (+/-)-Pseudovincadifformine and (+/-)-20-Epipseudovincadifformine". . p. 6076 - 6082. Retrieved 2007/10/02.