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

Base Information

• Chemical Name: (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid
• CAS No.: 127244-82-0
• Molecular Formula: C₂₆H₃₀N₂O₆Si
• Molecular Weight: 494.62
• Mol file: 127244-82-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic 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: 100.0%

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (83467-48-5) → (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid (127244-82-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo001223a

Reference yield: 95.0%

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester (127218-27-3) → (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid (127244-82-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(01)80556-6

Reference yield:

5'-O-(4-monomethoxytrityl)-2'-deoxythymidine (42926-80-7) → (2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid (127244-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole / dimethylformamide / 54 h / 20 °C

2: 100 percent / Amberlyst 15-H / methanol / 30 h / 20 °C

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

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; Amberlyst 15-H; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo001223a

upstream raw materials:

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

1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

5'-O-(4-monomethoxytrityl)-2'-deoxythymidine

1-[(2R,4S,5R)-5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

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

<6'-diethoxyphosphonate-3'-O-tert-butyldiphenylsilyl-6'-thio-(2'-pyridyl)-2',5',6'-trideoxy-β-D-ribo-hexofuranosyl>-1-thymine

(6'-diethoxyphosphonate-3'-O-tert-butyldiphenylsilyl-2',5',6'-trideoxy-β-D-ribo-hexofuranosyl)-1-thymine

6'-<(3'-azido-2',3',5',6'-tetradeoxy-β-D-ribo-hexofuranosyl)-1-thymine>-phosphonic acid