3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime

Base Information

• Chemical Name: 3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime
• CAS No.: 380615-25-8
• Molecular Formula: C₂₃H₃₃N₃O₅Si
• Molecular Weight: 459.618
• Mol file: 380615-25-8.mol

Synonyms:

Chemical Property of 3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime

There total 1 articles about 3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime 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:

O-benzylhydoxylamine hydrochloride (2687-43-6) + 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde (131118-61-1) → 3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime (380615-25-8)

Guidance literature:

With pyridine; at 100 ℃; for 12h;

DOI:10.1081/NCN-100002513

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime (380615-25-8) → 1-[5-(benzyloxyamino-methyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (291753-12-3)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; at 20 ℃; for 6h;

DOI:10.1081/NCN-100002513

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde O-benzyl-oxime (380615-25-8) → N-benzyloxy-2-[2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide (380615-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium cyanoborohydride / methanol; acetic acid / 6 h / 20 °C

2: O-(1H-benzotriazol-1-yl)-N,N,N'N'-tetramethyluronium BF₆^(1-); N-hydroxybenzotriazole / acetonitrile / 20 °C

3: tetra-n-butylammonium fluoride

With O-(1H-benzotriazol-1-yl)-N,N,N'N'-tetramethyluronium BF₆^(1-); tetrabutyl ammonium fluoride; sodium cyanoborohydride; benzotriazol-1-ol; In methanol; acetic acid; acetonitrile;

DOI:10.1081/NCN-100002513

upstream raw materials:

O-benzylhydoxylamine hydrochloride

3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

Downstream raw materials:

1-[5-(benzyloxyamino-methyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

N-benzyloxy-2-[2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-N-[3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-acetamide

C₅₆H₆₇N₅O₁₂Si