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

Base Information

Chemical Name:3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl ester
CAS No.:316808-06-7
Molecular Formula:C₃₀H₃₃NO₉
Molecular Weight:551.593
Hs Code.:

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

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

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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 dimethyl ester

There total 12 articles about 3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl 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: 59.0%

: 316808-05-6
3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 316808-06-7
3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: In ethanol; hexane; at 20 ℃; for 0.5h;
DOI:10.1016/j.bioorg.2003.09.001

Reference yield:

: 3430-31-7
3-bromo-2,6-dimethylpyridine

: 316808-06-7
3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 10 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

10: 59 percent / hexane; ethanol / 0.5 h / 20 °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:

: 316807-96-2
3-bromo-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine

: 316808-06-7
3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 59 percent / hexane; ethanol / 0.5 h / 20 °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; ethanol; hexane; acetonitrile;
DOI:10.1016/j.bioorg.2003.09.001