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

Base Information

• Chemical Name: (-)-(2R,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine
• CAS No.: 145913-69-5
• Molecular Formula: C₃₁H₃₂FN₃O₄SSi
• Molecular Weight: 589.763
• Mol file: 145913-69-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 5 articles about (-)-(2R,5S)-5-fluoro-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:

(2R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]oxathiolane-5-carbaldehyde (148774-90-7) → (-)-(2R,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-69-5)

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: 42.4 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 2 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-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / tetrahydrofuran / 0.5 h / Ambient temperature

2: 42.4 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 2 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 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,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine (145913-69-5)

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: 42.4 percent / trimethylsilyl triflate (TMSOTf) / 1,2-dichloro-ethane / 2 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:

(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

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

tert-Butyl-[(2R,5R)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-[1,3]oxathiolan-2-ylmethoxy]-diphenyl-silane

Downstream raw materials:

emtricitabine

Refernces