(2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine

Base Information

• Chemical Name: (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine
• CAS No.: 139757-73-6
• Molecular Formula: C₂₆H₃₁N₃O₄SSi
• Molecular Weight: 509.701

Synonyms:(2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine

Chemical Property of (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine

Chemical Property:

Purity/Quality:

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Technology Process of (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine

There total 6 articles about (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-acetylcytosine 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: 22.2%

N4-acetyl-O-trimethylsilylcytosine (54230-57-8) + (+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0) → (2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine (139757-74-7) + (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine (139757-73-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 1.5h; Ambient temperature;

DOI:10.1021/jm00054a001

Reference yield:

4-N-Acetylcytosine (14631-20-0) → (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine (139757-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: (NH₄)2SO₄ / 3 h / Heating

2: 22.2 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 1.5 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane;

DOI:10.1021/jm00054a001

Reference yield:

(+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane (139757-71-4) → (2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine (139757-73-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Pb(OAc)4 / ethyl acetate / 0.17 h / Ambient temperature

2: pyridinium dichromate (PDC) / dimethylformamide / 8 h / Ambient temperature

3: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

4: 22.2 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 1.5 h / Ambient temperature

With pyridine; lead(IV) acetate; dipyridinium dichromate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a001

upstream raw materials:

N⁴-acetyl-O-trimethylsilylcytosine

(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane

4-N-Acetylcytosine

(+)-(1'S,2R,5R)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(1',2'-dihydroxyethyl)-1,3-oxathiolane

Downstream raw materials:

(2R,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

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