{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

Base Information

• Chemical Name: {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester
• CAS No.: 357625-72-0
• Molecular Formula: C₄₀H₄₉N₃O₈Si
• Molecular Weight: 727.93

Synonyms:{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

Chemical Property of {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

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Technology Process of {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

There total 4 articles about {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester 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: 99.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + {1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester (357625-71-9) → {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester (357625-72-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; at 25 ℃; for 24h;

DOI:10.1081/NCN-100002082

Reference yield:

N4-[(allyloxy)carbonyl]-2'-deoxycytidine (102423-13-2) → {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester (357625-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 12 h / 25 °C

2: 99 percent / DBU / pyridine / 24 h / 25 °C

With 1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; N,N-dimethyl-formamide;

DOI:10.1081/NCN-100002082

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → {1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester (357625-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 24 h

2: pyridine / 24 h

With pyridine; 1H-imidazole; In N,N-dimethyl-formamide; 1: Etherification / 2: Etherification;

DOI:10.1016/S0040-4039(99)00748-0

upstream raw materials:

4,4'-dimethoxytrityl chloride

{1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid allyl ester

N⁴-[(allyloxy)carbonyl]-2'-deoxycytidine

tert-butyldimethylsilyl chloride

Downstream raw materials:

N⁴-(allyloxycarbonyl)-3'-O-(p,p'-dimethoxytrityl)-2'-deoxyacytidine 5'-(allyl N,N-diisopropylphosphoramidite)

N⁴-allyloxycarbonyl-3'-O-p,p'-dimethoxytrityl-2'-deoxycytidine

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