3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• CAS No.: 264128-06-5
• Molecular Formula: C₃₃H₃₆N₂O₉
• Molecular Weight: 604.657
• Mol file: 264128-06-5.mol

Synonyms:3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property of 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

There total 7 articles about 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-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: 100.0%

3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (264128-05-4) → 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (264128-06-5)

Guidance literature:

With formic acid; In acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4039(99)02209-1

Reference yield: 87.0%

C49H54N2O9Si → 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (264128-06-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b02555

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (264128-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

1.3: 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/jacs.9b02220

upstream raw materials:

3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

5'-O-trityluridine

uridine

Benzyloxymethyl chloride

Downstream raw materials:

Octadecyl-carbamic acid (2S,3S,4R,5R,6S)-2-(acetylamino-methyl)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-pyran-3-yl ester

Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

N-{(2S,3S,4R,5R,6S)-4,5-Bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl}-acetamide

1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Azidomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione