1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 151294-51-8
• Molecular Formula: C₄₅H₅₃N₂O₆PSi
• Molecular Weight: 776.985

Synonyms:

Chemical Property of 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-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,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione

There total 7 articles about 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-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:

5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine (120232-08-8) → 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione (151294-51-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / Ph₃P, diethyl azodicarboxylate / dioxane / 8 h / Ambient temperature

2: OsO₄, H₂O / dioxane / 0.25 h / Ambient temperature

3: aq. NaIO₄ / dioxane / 24 h / 20 - 25 °C

4: 100 percent / 2-methylbut-2-ene, sodium chlorite, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature

5: 96 percent / tetrahydrofuran / 16 h / Ambient temperature

6: 1.) n-BuLi / 1.) hexane, THF, r.t., 20 min, 2.) r.t., 4 h

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; water; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; tert-butyl alcohol;

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione (151294-51-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / Ph₃P, diethyl azodicarboxylate / dioxane / 8 h / Ambient temperature

2: OsO₄, H₂O / dioxane / 0.25 h / Ambient temperature

3: aq. NaIO₄ / dioxane / 24 h / 20 - 25 °C

4: 100 percent / 2-methylbut-2-ene, sodium chlorite, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature

5: 96 percent / tetrahydrofuran / 16 h / Ambient temperature

6: 1.) n-BuLi / 1.) hexane, THF, r.t., 20 min, 2.) r.t., 4 h

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; water; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; tert-butyl alcohol;

Reference yield:

1-[(2R,4S,5S)-4-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione (151294-47-2) → 1-{(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-[2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-tetrahydro-furan-2-yl}-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione (151294-51-8)

Guidance literature:

Multi-step reaction with 5 steps

1: OsO₄, H₂O / dioxane / 0.25 h / Ambient temperature

2: aq. NaIO₄ / dioxane / 24 h / 20 - 25 °C

3: 100 percent / 2-methylbut-2-ene, sodium chlorite, aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature

4: 96 percent / tetrahydrofuran / 16 h / Ambient temperature

5: 1.) n-BuLi / 1.) hexane, THF, r.t., 20 min, 2.) r.t., 4 h

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; water; In tetrahydrofuran; 1,4-dioxane; tert-butyl alcohol;

upstream raw materials:

Methyltriphenylphosphonium bromide

1-[(2R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyl)-5-methyl-1H-pyrimidine-2,4-dione

5'-O-(tert-butyldimethylsilyl)-3'-C-allyl-2',3'-dideoxythymidine

4-Methoxybenzyl alcohol

Downstream raw materials:

3'-O-Acetyl-3-(4-methoxybenzyl)-5'-{3-[(3'R)-5'-O-(tert-butyldimethylsilyl)-3-(4-methoxybenzyl)-3'-deoxythymidin-3'-yl]-2-oxopropyl}-5'-deoxythymidine

(E)-3'-O-Acetyl-3-(4-methoxybenzyl)-5'-{3-[(3'R)-5'-O-(tert-butyldimethylsilyl)-3-(4-methoxybenzyl)-3'-deoxythymidin-3'-yl]-2-oxopropylidene}-5'-deoxythymidine

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