1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 172280-74-9
• Molecular Formula: C₄₄H₅₇N₅O₇Si
• Molecular Weight: 796.051

Synonyms:

Chemical Property of 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 7 articles about 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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:

4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (172280-74-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dimethylsulfoxide

2: 65 percent / NaH / dimethylsulfoxide

3: 1.) BH₃, dimethylsulfide; 2.) sodium perborate

5: NaN₃

With sodium azide; sodium perborate; dimethylsulfide; borane; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78243-8

Reference yield:

3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine (139887-99-3) → 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (172280-74-9)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalylchloride, triethylamine / dimethylsulfoxide

2: triethylamine / dimethylsulfoxide

3: 65 percent / NaH / dimethylsulfoxide

4: 1.) BH₃, dimethylsulfide; 2.) sodium perborate

6: NaN₃

With sodium azide; sodium perborate; dimethylsulfide; Chloro-oxo-acetic acid; borane; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78243-8

Reference yield:

(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde (139888-01-0) → 1-[(2R,4S,5R)-5-((E)-7-Azido-hept-1-enyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (172280-74-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dimethylsulfoxide

2: 65 percent / NaH / dimethylsulfoxide

3: 1.) BH₃, dimethylsulfide; 2.) sodium perborate

5: NaN₃

With sodium azide; sodium perborate; dimethylsulfide; borane; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78243-8

upstream raw materials:

Methanesulfonic acid (E)-7-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-hept-6-enyl ester

4,4'-dimethoxytrityl chloride

3'-O-(tert-butyldimethylsilyl)-4'-(hydroxymethyl)-thymidine

(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

Downstream raw materials:

N-{(E)-7-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-hept-6-enyl}-2,2,2-trifluoro-acetamide

N-{(E)-7-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-hept-6-enyl}-2,2,2-trifluoro-acetamide

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