Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Base Information

• Chemical Name: Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester
• CAS No.: 343969-44-8
• Molecular Formula: C₃₄H₄₉NO₅
• Molecular Weight: 551.767

Synonyms:Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Chemical Property of Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

Chemical Property:

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Technology Process of Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

There total 4 articles about Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl 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: 25.0%

Pyridine-2-carboxylic acid (R)-3-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (343969-43-7) → Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (343969-44-8)

Guidance literature:

With selenium(IV) oxide; In dichloromethane; acetonitrile; at 45 ℃; for 18h;

DOI:10.1016/S0040-4039(01)00317-3

Reference yield:

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol (84985-78-4) → Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (343969-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.5 h / 20 °C

2: 20 percent / selenium dioxide / CH₂Cl₂; acetonitrile / 18 h / Heating

With selenium(IV) oxide; di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; toluene; acetonitrile; 1: Mitsunobu reaction;

Reference yield:

Calciferol (50-14-6) → Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (343969-44-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / KMnO₄

2: 39 percent / Ph₃P; diisopropyl azodicarboxylate

3: 25 percent / SeO₂ / CH₂Cl₂; acetonitrile / 18 h / 45 °C

With potassium permanganate; selenium(IV) oxide; di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; acetonitrile; 2: Mitsunobu reaction;

DOI:10.1016/S0040-4039(01)00317-3

upstream raw materials:

Pyridine-2-carboxylic acid (R)-3-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester

2-Picolinic acid

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol

Calciferol

Downstream raw materials:

(2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

(Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol

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