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

Base Information

• Chemical Name: (2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
• CAS No.: 667940-13-8
• Molecular Formula: C₂₀H₂₆N₂O₆S
• Molecular Weight: 422.502
• Mol file: 667940-13-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester 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: 67.0%

methanesulfonyl chloride (124-63-0) + (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 (667940-12-7) → (2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester (667940-13-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/ol0361507

Reference yield:

(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester (206554-22-5) → (2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester (667940-13-8)

Guidance literature:

Multi-step reaction with 8 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

With (-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; triethylamine; triphenylphosphine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0361507

Reference yield:

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (206761-38-8) → (2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester (667940-13-8)

Guidance literature:

Multi-step reaction with 9 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

With (-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; triethylamine; triphenylphosphine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;

DOI:10.1021/ol0361507

upstream raw materials:

methanesulfonyl chloride

(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

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

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

Downstream raw materials:

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

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

cytisine