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

Base Information

• Chemical Name: (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine
• CAS No.: 145913-71-9
• Molecular Formula: C₃₁H₃₂BrN₃O₄SSi
• Molecular Weight: 650.668

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

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

Chemical Property:

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

There total 6 articles about (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 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: 45.0%

(+)-(2R,5RS)-5-acetoxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolane (324015-67-0) + N-(5-Bromo-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide (149712-94-7) → (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-71-9) + (+)-(2R,5R)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145986-22-7)

Guidance literature:

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

DOI:10.1021/jm00054a001

Reference yield:

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde (148774-90-7) → (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-71-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

3: 45 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 1.5 h / Ambient temperature

With pyridine; dipyridinium dichromate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a001

Reference yield:

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid (139689-04-6) → (-)-(2R,5S)-5-bromo-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

2: 45 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 1.5 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/jm00054a001

upstream raw materials:

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

N-(5-Bromo-2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carboxylic acid

Downstream raw materials:

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

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