1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea

Base Information

• Chemical Name: 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea
• CAS No.: 259137-67-2
• Molecular Formula: C₄₃H₅₄N₂O₆Si₂
• Molecular Weight: 751.083
• Mol file: 259137-67-2.mol

Synonyms:

Chemical Property of 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea

There total 7 articles about 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea 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:

tert-butylchlorodiphenylsilane (58479-61-1) → 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea (259137-67-2)

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: 86 percent / toluene; dimethylformamide / 18 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:

1,4-anhydro-D-ribitol (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-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea (259137-67-2)

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: 86 percent / toluene; dimethylformamide / 18 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

Reference yield:

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol (215031-98-4) → 1-[(3R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea (259137-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.04 g / SOCl₂; pyridine / 20 °C

2: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

3: 87 percent / imidazole / dimethylformamide / 18 h / 70 °C

4: 93 percent / H₂ / Pd/C / ethyl acetate; ethanol / 6 h / 1292.87 Torr

5: 86 percent / toluene; dimethylformamide / 18 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: Cyclization / 2: Ring cleavage / 3: Substitution / 4: Reduction / 5: Addition;

DOI:10.1080/07328319908044614

upstream raw materials:

tert-butylchlorodiphenylsilane

3-methoxy-2-methylacryloyl chloride

1,4-anhydro-D-ribitol

2(R)-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-(3S,4S)-diol

Downstream raw materials:

Benzoic acid (2R,3S,4R)-3-methanesulfonyloxy-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl>-D-arabinitol