4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Base Information

Chemical Name:4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran
CAS No.:259137-60-5
Molecular Formula:C₄₃H₅₄N₂O₆Si₂
Molecular Weight:751.083
Hs Code.:

4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Synonyms:4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

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Chemical Property of 4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

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Technology Process of 4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

There total 8 articles about 4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran 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: 93.0%

: 57796-78-8,928778-13-6
(3-ethoxy-acryloyl)isocyanate

: 259137-59-2
2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)-4(R)-aminotetrahydrofuran

: 259137-60-5
4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: In toluene; at 0 - 20 ℃; for 2.5h;
DOI:10.1080/07328319908044614

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 259137-60-5
4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

2: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

3: 93 percent / toluene / 2.5 h / 0 - 20 °C

With 1H-imidazole; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Reduction / 3: Addition;
DOI:10.1080/07328319908044614

Reference yield:

: 491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9
1,4-anhydro-D-ribitol

: 259137-60-5
4(R)-[{(3-ethoxy-1-oxo-2-propenyl)aminocarbonyl}amino]-2(R)-(tert-butyldimethylsilyloxymethyl)-3(S)-(tert-butyldiphenylsilyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

5: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

6: 93 percent / toluene / 2.5 h / 0 - 20 °C

With pyridine; 1H-imidazole; thionyl chloride; sodium azide; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Substitution / 5: Reduction / 6: Addition;
DOI:10.1080/07328319908044614