N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine
• CAS No.: 201853-30-7
• Molecular Formula: C₃₃H₃₅N₃O₄Si
• Molecular Weight: 565.744

Synonyms:N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine

Chemical Property of N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine

There total 7 articles about N⁴-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine 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: 89.0%

4-N-benzoylcytosine (26661-13-2) + α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate (201853-28-3) → N4-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine (201853-30-7)

Guidance literature:

4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 18h; Heating;

α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/jo991212l

Reference yield: 68.0%

4-N-benzoylcytosine (26661-13-2) + α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride (201853-29-4) → N4-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine (201853-30-7)

Guidance literature:

4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 18h; Heating;

α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride; In chloroform; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/jo991212l

Reference yield:

(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane (153861-49-5) → N4-benzoyl-1-(5-O-tert-butyldiphenylsilyl-2,3-dideoxy-2,3-endo-methylene-α/β-D-pentofuranosyl)cytosine (201853-30-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMSO; oxalic chloride; Et₃N / CH₂Cl₂ / 0.25 h / -78 °C

2.1: 0.1 N HCl / dioxane / 4 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 87 percent / pyridine / 0.5 h

5.1: HCl / diethyl ether / 0.17 h / -10 °C

6.1: HMDS; (NH₄)2SO₄ / 18 h / Heating

6.2: 68 percent / CHCl₃ / 3 h / 20 °C

With pyridine; hydrogenchloride; ammonium sulfate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 1,4-dioxane; pyridine; diethyl ether; dichloromethane; 1.1: Oxidation / 2.1: Cyclization / 3.1: silylation / 4.1: Acetylation / 5.1: Substitution / 6.1: silylation / 6.2: Condensation;

DOI:10.1021/jo991212l

upstream raw materials:

4-N-benzoylcytosine

α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane

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