3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

Base Information

• Chemical Name: 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil
• CAS No.: 1332758-07-2
• Molecular Formula: C₂₉H₄₈N₂O₇Si₂
• Molecular Weight: 592.88

Synonyms:3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

Chemical Property of 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

Chemical Property:

Purity/Quality:

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Technology Process of 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

There total 3 articles about 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil 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: 83.0%

3-(benzyloxymethyl)-1-[2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-04-9) → 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-07-2)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 0 ℃; for 7h; Inert atmosphere;

DOI:10.1021/ol202124b

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / tetrahydrofuran; water / 7 h / 0 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ol202124b

Reference yield:

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine (64898-15-3) → 3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil (1332758-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / tetrahydrofuran; water / 7 h / 0 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ol202124b

upstream raw materials:

3-(benzyloxymethyl)-1-[2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribo-pentofuranosyl]uracil

Benzyloxymethyl chloride

2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine

Downstream raw materials:

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-β-D-ribopentofuranosyl]uracil

(Z)-3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-4,5-dehydro-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil

3-(benzyloxymethyl)-1-[2,3-di-O-(tert-butyldimethylsilyl)-5-deoxy-5-iodo-β-D-ribopentofuranosyl]uracil

2',3'-bis(O-tert-butyldimethylsilyl)-3-(benzyloxymethyl)uridine-5'-aldehyde

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