(15S)-19,20-Didehydro-17α-methyl-21-oxo-18-oxayohimban-16β-carbaldehyde

Base Information

• Chemical Name: (15S)-19,20-Didehydro-17α-methyl-21-oxo-18-oxayohimban-16β-carbaldehyde
• CAS No.: 77513-45-2
• Molecular Formula: C₂₀H₂₀N₂O₃
• Molecular Weight: 336.39
• Mol file: 77513-45-2.mol

Synonyms:(10R,11S,11aS,12aS)-10-Methyl-7-oxo-5,6,10,11,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carbaldehyde;

Chemical Property of (15S)-19,20-Didehydro-17α-methyl-21-oxo-18-oxayohimban-16β-carbaldehyde

Chemical Property:

• Melting Point: 191 - 194 °C
• PSA: 62.40000
• LogP: 2.66920

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (15S)-19,20-Didehydro-17α-methyl-21-oxo-18-oxayohimban-16β-carbaldehyde

There total 10 articles about (15S)-19,20-Didehydro-17α-methyl-21-oxo-18-oxayohimban-16β-carbaldehyde 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: 52.0%

(10R,11R,11aS,12aS)-10-Hydroxy-11-vinyl-5,6,10,11,11a,12,12a,13-octahydro-9-oxa-6a,13-diaza-indeno[2,1-a]anthracen-7-one → naucleidinal (77513-45-2,77513-46-3)

Guidance literature:

With pyridine; at 110 ℃; for 5h;

DOI:10.1248/cpb.44.2192

Reference yield: 47.0%

(–)-naucleaoral B → C20H20N2O3 + naucleidinal (77513-45-2,77513-46-3)

Guidance literature:

With pyridine; In water; at 100 ℃; for 7h; Inert atmosphere;

DOI:10.1002/chem.202104052

Reference yield:

C20H26O4SSi → C20H20N2O3 + naucleidinal (77513-45-2,77513-46-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: silver nitrate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: 9-BBN triflate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.2: 38 h / 20 °C / Inert atmosphere

3.1: trimethyl phosphite / 1,2-dichloro-benzene / 0.28 h / Inert atmosphere; Reflux

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

5.1: acetic acid; sodium cyanoborohydride / methanol / 60 h / 20 °C / Inert atmosphere

6.1: toluene / 48 h / 70 °C

7.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / -20 - 0 °C / Inert atmosphere

8.1: pyridine / water / 7 h / 100 °C / Inert atmosphere

With pyridine; trimethyl phosphite; tetrabutyl ammonium fluoride; sodium cyanoborohydride; silver nitrate; acetic acid; trifluoroacetic acid; 9-BBN triflate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1,2-dichloro-benzene; toluene;

DOI:10.1002/chem.202104052

upstream raw materials:

strictosamide

(-)-secologanin aglucone-O-silyl ether