1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine

Base Information

• Chemical Name: 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine
• CAS No.: 138866-76-9
• Molecular Formula: C₃₃H₄₃N₃O₆Si
• Molecular Weight: 605.806

Synonyms:1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine

Chemical Property of 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine

Chemical Property:

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Technology Process of 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine

There total 4 articles about 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine 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%

2-O-trimethylsilyl-N4-isobutyrylcytosine (138866-74-7) + methyl 5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside (138866-67-8) → 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N4-isobutyrylcytosine (138866-76-9) + 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)-N4-isobutyrylcytosine (138866-75-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -35 ℃; for 1.5h; Yields of byproduct given;

DOI:10.1002/ardp.2503241203

Reference yield:

(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran (130144-85-3) → 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N4-isobutyrylcytosine (138866-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 5 °C

2: 25 percent / tri-n-butyltin hydride, AIBN / toluene / 1 h / 80 °C

3: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1.5 h / -35 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; toluene; acetonitrile;

DOI:10.1002/ardp.2503241203

Reference yield:

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside (138866-64-5) → 1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N4-isobutyrylcytosine (138866-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 25 percent / tri-n-butyltin hydride, AIBN / toluene / 1 h / 80 °C

2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1.5 h / -35 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In toluene; acetonitrile;

DOI:10.1002/ardp.2503241203

upstream raw materials:

2-O-trimethylsilyl-N⁴-isobutyrylcytosine

methyl 5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranoside

(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran

methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-phenoxythiocarbonyl-α-D-erythro-pentofuranoside

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