(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester
CAS No.:339178-45-9
Molecular Formula:C₂₇H₃₂N₂O₆Si
Molecular Weight:508.646
Hs Code.:

(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

Synonyms:(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

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Technology Process of (2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

There total 8 articles about (2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl 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: 92.0%

: 339178-44-8
(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 339178-45-9
(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: In methanol; hexane; benzene; at 20 ℃; for 10h;
DOI:10.1021/jo001223a

Reference yield:

: 124680-51-9
(2R,4R,5R)-1-[5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-hydroxytetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 339178-45-9
(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / imidazole / dimethylformamide / 1.5 h / Heating

2: 100 percent / Amberlyst 15-H / methanol / 37 h / 20 °C

3: 100 percent / 2,2,6,6-tetramethyl-1-piperidinyl-oxy; iodobenzene diacetate / CH₂Cl₂ / 2 h / 20 °C

4: 92 percent / benzene; methanol; hexane / 10 h / 20 °C

With 1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; Amberlyst 15-H; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo001223a

Reference yield:

: 42926-80-7
5'-O-(4-monomethoxytrityl)-2'-deoxythymidine

: 339178-45-9
(2S,3R,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / Py / 18 h / 0 °C

2: 91 percent / NaOH / ethanol; H₂O / 2 h / Heating

3: 100 percent / NaOH / ethanol; H₂O / 3 h / Heating

4: 94 percent / imidazole / dimethylformamide / 1.5 h / Heating

5: 100 percent / Amberlyst 15-H / methanol / 37 h / 20 °C

6: 100 percent / 2,2,6,6-tetramethyl-1-piperidinyl-oxy; iodobenzene diacetate / CH₂Cl₂ / 2 h / 20 °C

7: 92 percent / benzene; methanol; hexane / 10 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; Amberlyst 15-H; In methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo001223a