(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

Base Information

• Chemical Name: (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine
• CAS No.: 667940-15-0
• Molecular Formula: C₁₉H₂₀N₂O₃
• Molecular Weight: 324.379
• Mol file: 667940-15-0.mol

Synonyms:(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

Chemical Property of (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

There total 11 articles about (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine 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: 50.0%

(6R,7R,9R)-(+)-N-benzyloxycarbonyl-5,6-dihydro-cytisine (667940-14-9) → (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine (667940-15-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 110 ℃; for 4h;

DOI:10.1021/ol0361507

Reference yield:

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (206761-38-8) → (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine (667940-15-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C

1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis

1.3: 76 percent / aq. NaOH; aq. H₂O₂ / 3 h / Heating

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 87 percent / NaN₃ / dimethylformamide / 2 h / 80 °C

4.1: Ph₃P / tetrahydrofuran

4.2: 66 percent / H₂O

5.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

6.1: 79 percent / Cl₂Ru(CHPh)(PCy₃)2 / CH₂Cl₂ / 12 h / Heating

7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C

8.1: 67 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C

10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C

With (-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; sodium hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;

DOI:10.1021/ol0361507

Reference yield:

(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester (206554-22-5) → (6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine (667940-15-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C

1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis

1.3: 76 percent / aq. NaOH; aq. H₂O₂ / 3 h / Heating

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 87 percent / NaN₃ / dimethylformamide / 2 h / 80 °C

4.1: Ph₃P / tetrahydrofuran

4.2: 66 percent / H₂O

5.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

6.1: 79 percent / Cl₂Ru(CHPh)(PCy₃)2 / CH₂Cl₂ / 12 h / Heating

7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C

8.1: 67 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C

10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C

With (-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; sodium hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0361507

upstream raw materials:

(6R,7R,9R)-(+)-N-benzyloxycarbonyl-5,6-dihydro-cytisine

(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester

Downstream raw materials:

cytisine

Refernces