3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine

Base Information

• Chemical Name: 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine
• CAS No.: 154230-34-9
• Molecular Formula: C₃₆H₄₄N₂O₇Si
• Molecular Weight: 644.84

Synonyms:3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property of 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine

Chemical Property:

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Technology Process of 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine

There total 4 articles about 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine 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: 90.0%

[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-acetic acid ethyl ester (154230-33-8) → 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine (154230-34-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 23 ℃;

DOI:10.1021/jo00081a003

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine (154230-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 76 percent / NaH / dimethylformamide / 0 - 23 °C

3: 90 percent / NaBH₄ / methanol / 0 - 23 °C

With sodium tetrahydroborate; sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00081a003

Reference yield:

5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) → 3-((Benzyloxy)methyl)-3'-O-(2-hydroxyethyl)-5'-O-(tert-butyldiphenylsilyl)thymidine (154230-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 76 percent / NaH / dimethylformamide / 0 - 23 °C

3: 90 percent / NaBH₄ / methanol / 0 - 23 °C

With sodium tetrahydroborate; sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00081a003

upstream raw materials:

[(2R,3S,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yloxy]-acetic acid ethyl ester

Benzyloxymethyl chloride

5'-O-tert-butyldiphenylsilylthymidine

5'-O-tert-butyldiphenylsilyl-N³-benzyloxymethyl-2'-deoxythymidine

Downstream raw materials:

C₆₀H₆₆N₄O₁₃Si

Benzoic acid (2S,3S,5R)-2-{2-[(2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-ethoxy}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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