1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione
• CAS No.: 903570-39-8
• Molecular Formula: C₆₀H₅₈N₂O₉S
• Molecular Weight: 983.195
• Mol file: 903570-39-8.mol

Synonyms:1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione

Chemical Property of 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-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-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione

There total 5 articles about 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-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: 70.0%

1-{(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione (903570-47-8) + 3,4-dibenzyloxybenzyl chloride (1699-59-8) → 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione (903570-39-8)

Guidance literature:

With sodium hydride; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1055/s-2006-933147

Reference yield:

1-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione (903570-37-6) → 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione (903570-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

2: 70 percent / NaH; NaI / dimethylformamide / 18 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-933147

Reference yield:

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → 1-{(2R,4S,5R)-5-(3,4-Bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione (903570-39-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / DMAP; pyridine / 12 h / 20 °C

2: 90 percent / tributylphosphine; 1,1'-(azodicarbonyl)dipiperidine / benzene / 18 h / 20 °C

3: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

4: 70 percent / NaH; NaI / dimethylformamide / 18 h / 20 °C

With pyridine; dmap; tributylphosphine; tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; N,N-dimethyl-formamide; benzene; 2: Mitsunobu reaction;

DOI:10.1055/s-2006-933147

upstream raw materials:

1-{(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione

3,4-dibenzyloxybenzyl chloride

1-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-3-(2-phenylsulfanyl-ethyl)-1H-pyrimidine-2,4-dione

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Downstream raw materials:

3-(2-Benzenesulfonyl-ethyl)-1-[(2R,4S,5R)-5-(3,4-bis-benzyloxy-benzyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

3-(2-Benzenesulfonyl-ethyl)-1-{(2R,4S,5R)-5-(3,4-bis-benzyloxy-benzyloxymethyl)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione