3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-trityloxymethyl-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-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• CAS No.: 264128-05-4
• Molecular Formula: C₅₂H₅₀N₂O₉
• Molecular Weight: 846.977

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

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

Chemical Property:

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

There total 3 articles about 3-Benzyloxymethyl-1-((2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-trityloxymethyl-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: 40.0%

Benzyloxymethyl chloride (3587-60-8) + 5'-O-trityluridine (6554-10-5) → 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)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

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

Reference yield:

trityl chloride (76-83-5) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DMAP; pyridine

2: 40 percent / NaH; NBu₄I / dimethylformamide

With pyridine; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; 1: Alkylation / 2: Alkylation;

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

Reference yield:

uridine (58-96-8) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DMAP; pyridine

2: 40 percent / NaH; NBu₄I / dimethylformamide

With pyridine; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; 1: Alkylation / 2: Alkylation;

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

upstream raw materials:

Benzyloxymethyl chloride

5'-O-trityluridine

trityl chloride

uridine

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

3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,4aS,6S,7R,8R,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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

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