3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid

Base Information

• Chemical Name: 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid
• CAS No.: 316808-05-6
• Molecular Formula: C₂₈H₂₉NO₉
• Molecular Weight: 523.54

Synonyms:3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid

Chemical Property of 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid

There total 11 articles about 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid 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:

3-bromo-2,6-dimethylpyridine (3430-31-7) → 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid (316808-05-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 29.8 g / KMnO₄ / H₂O / 12 h / 90 °C

2: thionyl chloride / 4 h / Heating

3: 25.0 g / 1 h / Heating

4: 77 percent / NaBH₄ / ethanol / 16 h / Heating

5: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 - 20 °C

6: 36 percent / n-BuLi / hexane; tetrahydrofuran / 2.5 h / -78 - 20 °C

7: 60 percent / pyridine; triethylamine; methanesulfonyl chloride / 4 h / 0 - 20 °C

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

9: 1.58 g / TEMPO; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 35 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium tetrahydroborate; potassium permanganate; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; phosphate buffer; ethanol; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/j.bioorg.2003.09.001

Reference yield:

{6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol (316808-04-5) → 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid (316808-05-6)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 35 ℃;

DOI:10.1016/j.bioorg.2003.09.001

Reference yield:

3-bromo-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine (316807-96-2) → 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid (316808-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 36 percent / n-BuLi / hexane; tetrahydrofuran / 2.5 h / -78 - 20 °C

2: 60 percent / pyridine; triethylamine; methanesulfonyl chloride / 4 h / 0 - 20 °C

3: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

4: 1.58 g / TEMPO; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 35 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; n-butyllithium; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; phosphate buffer; hexane; acetonitrile;

DOI:10.1016/j.bioorg.2003.09.001

upstream raw materials:

{6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol

3-bromo-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine

2,6-bis-(tetr-butyl-dimethyl-silanyloxymethyl)-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridine

1S-[2,6-bis-(tetr-butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-3S,4R,5-tris-(4-methoxy-benzyloxy)-pentan-1-ol

Downstream raw materials:

3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl ester

3-{5R-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4S-hydroxy-tetrahydro-furan-2R-yl}-pyridine-2,6-dicarboxylic acid dimethyl ester

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